HU176607B - Process for producing compounds of optical activity - Google Patents

Process for producing compounds of optical activity Download PDF

Info

Publication number: HU176607B
Authority: HU; Hungary
Prior art keywords: optically active; group; phenyl; alkyl; optical activity
Prior art date: 1973-04-13

Application number

HU74SA2625A

Other languages

English (en)

Hungarian (hu)

Inventor

Matteo Giongo

Walter Marconi

Nicola Palladino

Gregorio Francesco Di

Original Assignee

Snam Progetti

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1973-04-13

Filing date

1974-04-12

Publication date

1981-03-28

1974-04-12 Application filed by Snam Progetti filed Critical Snam Progetti

1981-03-28 Publication of HU176607B publication Critical patent/HU176607B/hu

Links

238000000034 method Methods 0.000 title claims abstract description 10
150000001875 compounds Chemical class 0.000 title claims description 17
230000003287 optical effect Effects 0.000 title description 22
239000001257 hydrogen Substances 0.000 claims abstract description 8
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
125000000217 alkyl group Chemical group 0.000 claims abstract description 6
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052782 aluminium Inorganic materials 0.000 claims abstract description 5
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 4
150000001412 amines Chemical class 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 10
150000002466 imines Chemical class 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 5
150000001298 alcohols Chemical class 0.000 claims description 4
150000002576 ketones Chemical class 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
150000003335 secondary amines Chemical class 0.000 claims description 3
150000003141 primary amines Chemical class 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 abstract description 6
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 abstract description 5
238000002360 preparation method Methods 0.000 abstract description 4
239000007858 starting material Substances 0.000 abstract description 4
229910000086 alane Inorganic materials 0.000 abstract description 3
229910052757 nitrogen Inorganic materials 0.000 abstract 2
125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
CWKYHZMWPLSOFA-UHFFFAOYSA-N 3-methyl-1-phenyl-2,5-dihydrophosphole Chemical compound C1C(C)=CCP1C1=CC=CC=C1 CWKYHZMWPLSOFA-UHFFFAOYSA-N 0.000 abstract 1
ZFAGOADKDXXTSV-UHFFFAOYSA-N 3-methylpentan-2-amine Chemical compound CCC(C)C(C)N ZFAGOADKDXXTSV-UHFFFAOYSA-N 0.000 abstract 1
229910018509 Al—N Inorganic materials 0.000 abstract 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
125000002877 alkyl aryl group Chemical group 0.000 abstract 1
XPNGNIFUDRPBFJ-UHFFFAOYSA-N alpha-methylbenzylalcohol Natural products CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 abstract 1
125000003710 aryl alkyl group Chemical group 0.000 abstract 1
125000003118 aryl group Chemical group 0.000 abstract 1
239000000460 chlorine Chemical group 0.000 abstract 1
229910052801 chlorine Inorganic materials 0.000 abstract 1
125000005842 heteroatom Chemical group 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
SASNBVQSOZSTPD-UHFFFAOYSA-N n-methylphenethylamine Chemical group CNCCC1=CC=CC=C1 SASNBVQSOZSTPD-UHFFFAOYSA-N 0.000 description 9
-1 alcohols Chemical class 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
239000002904 solvent Substances 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
229910010082 LiAlH Inorganic materials 0.000 description 3
238000009876 asymmetric hydrogenation reaction Methods 0.000 description 3
239000000284 extract Substances 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000003513 alkali Substances 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
SPRIOUNJHPCKPV-UHFFFAOYSA-N hydridoaluminium Chemical compound [AlH] SPRIOUNJHPCKPV-UHFFFAOYSA-N 0.000 description 2
230000006698 induction Effects 0.000 description 2
229910052987 metal hydride Inorganic materials 0.000 description 2
150000004681 metal hydrides Chemical class 0.000 description 2
150000002923 oximes Chemical class 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 2
239000011734 sodium Substances 0.000 description 2
238000006276 transfer reaction Methods 0.000 description 2
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
WGTASENVNYJZBK-UHFFFAOYSA-N 3,4,5-trimethoxyamphetamine Chemical compound COC1=CC(CC(C)N)=CC(OC)=C1OC WGTASENVNYJZBK-UHFFFAOYSA-N 0.000 description 1
RBMUAGDCCJDQLE-UHFFFAOYSA-N 5-methyl-2-propan-2-ylcyclohexan-1-amine Chemical compound CC(C)C1CCC(C)CC1N RBMUAGDCCJDQLE-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
239000002879 Lewis base Substances 0.000 description 1
TXOFSCODFRHERQ-UHFFFAOYSA-N N,N-Dimethylphenethylamine Chemical compound CN(C)CCC1=CC=CC=C1 TXOFSCODFRHERQ-UHFFFAOYSA-N 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
235000004279 alanine Nutrition 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
238000011914 asymmetric synthesis Methods 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
150000002118 epoxides Chemical class 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
150000007527 lewis bases Chemical class 0.000 description 1
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Inorganic materials [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 1
SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
229910000103 lithium hydride Inorganic materials 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
229960002221 methylephedrine Drugs 0.000 description 1
230000002906 microbiologic effect Effects 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
QKYWADPCTHTJHQ-UHFFFAOYSA-N n,2-dimethylpropan-1-amine Chemical compound CNCC(C)C QKYWADPCTHTJHQ-UHFFFAOYSA-N 0.000 description 1
MYWUZJCMWCOHBA-UHFFFAOYSA-N n-methyl-1-phenylpropan-2-amine Chemical compound CNC(C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-UHFFFAOYSA-N 0.000 description 1
WIBADEXUNPVVIP-UHFFFAOYSA-N n-methyl-2-phenylethanamine;hydrochloride Chemical compound Cl.CNCCC1=CC=CC=C1 WIBADEXUNPVVIP-UHFFFAOYSA-N 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
230000006340 racemization Effects 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
150000007659 semicarbazones Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000006257 total synthesis reaction Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
- C07C209/52—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of imines or imino-ethers
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/36—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by hydrogenation of carbon-to-carbon unsaturated bonds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/069—Aluminium compounds without C-aluminium linkages
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/505—Preparation; Separation; Purification; Stabilisation
- C07F9/509—Preparation; Separation; Purification; Stabilisation by reduction of pentavalent phosphorus derivatives, e.g. -P=X with X = O, S, Se or -P-Hal2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Oil, Petroleum & Natural Gas (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Hydrogenated Pyridines (AREA)

HU74SA2625A 1973-04-13 1974-04-12 Process for producing compounds of optical activity HU176607B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT22954/73A IT987071B (it)	1973-04-13	1973-04-13	Idrogenazione asimmetrica a mez zo di derivati otticamente atti vi dell idroro di alluminio

Publications (1)

Publication Number	Publication Date
HU176607B true HU176607B (en)	1981-03-28

Family

ID=11202251

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU74SA2625A HU176607B (en)	1973-04-13	1974-04-12	Process for producing compounds of optical activity

Country Status (17)

Country	Link
JP (1)	JPS5929045B2 (fr)
BE (1)	BE813718A (fr)
CA (1)	CA1021801A (fr)
CH (1)	CH606032A5 (fr)
CS (1)	CS203074B2 (fr)
DD (1)	DD113740A5 (fr)
DK (1)	DK137922B (fr)
FR (1)	FR2225397B1 (fr)
GB (1)	GB1460781A (fr)
HU (1)	HU176607B (fr)
IT (1)	IT987071B (fr)
LU (1)	LU69850A1 (fr)
NL (1)	NL7404845A (fr)
NO (1)	NO142864C (fr)
SE (1)	SE419550B (fr)
YU (1)	YU96574A (fr)
ZA (1)	ZA742324B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2714721A1 (de) *	1976-05-17	1977-12-01	Texas Alkyls Inc	Reduktion von triphenylphosphinoxid zu triphenylphosphin
US5189208A (en) *	1991-07-01	1993-02-23	Ethyl Corporation	Ibuprofen resolution
EP1846350A2 (fr) *	2005-01-27	2007-10-24	University of Nottingham	Procede ameliore de preparation d'alcools secondaires enrichis enantiomeriquement par l'addition de reactifs d'organo-aluminium sur des composes carbonyle

1973
- 1973-04-13 IT IT22954/73A patent/IT987071B/it active
1974
- 1974-04-04 NO NO741246A patent/NO142864C/no unknown
- 1974-04-08 CH CH487074A patent/CH606032A5/xx not_active IP Right Cessation
- 1974-04-08 YU YU00965/74A patent/YU96574A/xx unknown
- 1974-04-09 GB GB1578174A patent/GB1460781A/en not_active Expired
- 1974-04-09 NL NL7404845A patent/NL7404845A/xx active Search and Examination
- 1974-04-10 SE SE7404949A patent/SE419550B/xx not_active IP Right Cessation
- 1974-04-10 ZA ZA00742324A patent/ZA742324B/xx unknown
- 1974-04-10 FR FR7412543A patent/FR2225397B1/fr not_active Expired
- 1974-04-10 DK DK202374AA patent/DK137922B/da not_active IP Right Cessation
- 1974-04-11 CA CA197,532A patent/CA1021801A/fr not_active Expired
- 1974-04-11 DD DD177852A patent/DD113740A5/xx unknown
- 1974-04-12 CS CS742668A patent/CS203074B2/cs unknown
- 1974-04-12 JP JP49040466A patent/JPS5929045B2/ja not_active Expired
- 1974-04-12 HU HU74SA2625A patent/HU176607B/hu unknown
- 1974-04-12 BE BE143208A patent/BE813718A/fr not_active IP Right Cessation
- 1974-04-12 LU LU69850A patent/LU69850A1/xx unknown

Also Published As

Publication number	Publication date
LU69850A1 (fr)	1974-07-18
NL7404845A (fr)	1974-10-15
IT987071B (it)	1975-02-20
ZA742324B (en)	1975-04-30
FR2225397A1 (fr)	1974-11-08
DK137922B (da)	1978-06-05
CS203074B2 (en)	1981-02-27
DE2416396B2 (de)	1977-02-17
DK137922C (fr)	1978-10-30
CA1021801A (fr)	1977-11-29
JPS5076002A (fr)	1975-06-21
GB1460781A (en)	1977-01-06
BE813718A (fr)	1974-07-31
NO142864B (no)	1980-07-28
AU6753874A (en)	1975-10-09
YU96574A (en)	1982-05-31
CH606032A5 (fr)	1978-10-13
NO741246L (no)	1974-10-15
JPS5929045B2 (ja)	1984-07-18
DD113740A5 (fr)	1975-06-20
DE2416396A1 (de)	1974-10-31
SE419550B (sv)	1981-08-10
FR2225397B1 (fr)	1976-06-25
NO142864C (no)	1980-11-05

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