NL9101623A - Werkwijze voor de bereiding van een alcohol. - Google Patents

Werkwijze voor de bereiding van een alcohol. Download PDF

Info

Publication number: NL9101623A
Authority: NL; Netherlands
Prior art keywords: disubstituted; alcohol; amide; amino acid; sodium
Prior art date: 1991-09-26

Application number

NL9101623A

Other languages

English (en)

Dutch (nl)

Original Assignee

Dsm Nv

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.)

1991-09-26

Filing date

1991-09-26

Publication date

1993-04-16

1991-09-26 Application filed by Dsm Nv filed Critical Dsm Nv

1991-09-26 Priority to NL9101623A priority Critical patent/NL9101623A/nl

1992-09-22 Priority to EP92202911A priority patent/EP0534553B1/de

1992-09-22 Priority to JP4252676A priority patent/JPH05201936A/ja

1992-09-22 Priority to AT92202911T priority patent/ATE128456T1/de

1992-09-22 Priority to DE69205107T priority patent/DE69205107T2/de

1992-09-25 Priority to US07/950,713 priority patent/US5276190A/en

1993-04-16 Publication of NL9101623A publication Critical patent/NL9101623A/nl

Links

LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 20
238000004519 manufacturing process Methods 0.000 title description 2
238000000034 method Methods 0.000 claims abstract description 37
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract description 19
150000001408 amides Chemical class 0.000 claims abstract description 19
229910052708 sodium Inorganic materials 0.000 claims abstract description 19
239000011734 sodium Substances 0.000 claims abstract description 19
238000006243 chemical reaction Methods 0.000 claims abstract description 12
239000002904 solvent Substances 0.000 claims abstract description 7
238000002360 preparation method Methods 0.000 claims abstract description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 25
238000010992 reflux Methods 0.000 claims description 5
150000001413 amino acids Chemical class 0.000 abstract description 7
230000003287 optical effect Effects 0.000 abstract description 2
150000001414 amino alcohols Chemical class 0.000 abstract 2
230000014759 maintenance of location Effects 0.000 abstract 1
-1 2-phenethyl Chemical group 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
235000001014 amino acid Nutrition 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
229910000085 borane Inorganic materials 0.000 description 3
239000013078 crystal Substances 0.000 description 3
230000003301 hydrolyzing effect Effects 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
FGMZLSIURNPYDT-UHFFFAOYSA-N 2-anilinobutan-1-ol Chemical compound CCC(CO)NC1=CC=CC=C1 FGMZLSIURNPYDT-UHFFFAOYSA-N 0.000 description 2
239000002262 Schiff base Substances 0.000 description 2
150000004753 Schiff bases Chemical class 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
239000012071 phase Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000758 substrate Substances 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
JTLVRVHSLGHAJZ-UHFFFAOYSA-N 1-anthracen-1-yl-2,2,2-trifluoroethanol Chemical compound C1=CC=C2C=C3C(C(O)C(F)(F)F)=CC=CC3=CC2=C1 JTLVRVHSLGHAJZ-UHFFFAOYSA-N 0.000 description 1
FDCJXHIWLITAFB-UHFFFAOYSA-N 2-anilinobutanamide Chemical compound CCC(C(N)=O)NC1=CC=CC=C1 FDCJXHIWLITAFB-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 description 1
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
229910010084 LiAlH4 Inorganic materials 0.000 description 1
241000187469 Mycobacterium neoaurum Species 0.000 description 1
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
230000002411 adverse Effects 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001370 alpha-amino acid derivatives Chemical class 0.000 description 1
235000008206 alpha-amino acids Nutrition 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000005219 aminonitrile group Chemical group 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
230000007071 enzymatic hydrolysis Effects 0.000 description 1
238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012634 fragment Substances 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000007789 gas Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
125000006301 indolyl methyl group Chemical group 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000003446 ligand Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
125000005394 methallyl group Chemical group 0.000 description 1
244000005700 microbiome Species 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Chemical group 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
239000013558 reference substance Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000003579 shift reagent Substances 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NL9101623A 1991-09-26 1991-09-26 Werkwijze voor de bereiding van een alcohol. NL9101623A (nl)

Priority Applications (6)

Application Number	Priority Date	Filing Date	Title
NL9101623A NL9101623A (nl)	1991-09-26	1991-09-26	Werkwijze voor de bereiding van een alcohol.
EP92202911A EP0534553B1 (de)	1991-09-26	1992-09-22	Verfahren zur Herstellung eines Alpha-Amino-Alkohols
JP4252676A JPH05201936A (ja)	1991-09-26	1992-09-22	α，α−２置換−α−アミノアルコールの製法
AT92202911T ATE128456T1 (de)	1991-09-26	1992-09-22	Verfahren zur herstellung eines alpha-amino- alkohols.
DE69205107T DE69205107T2 (de)	1991-09-26	1992-09-22	Verfahren zur Herstellung eines Alpha-Amino-Alkohols.
US07/950,713 US5276190A (en)	1991-09-26	1992-09-25	Method for the preparation of an alcohol

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL9101623A NL9101623A (nl)	1991-09-26	1991-09-26	Werkwijze voor de bereiding van een alcohol.
NL9101623		1991-09-26

Publications (1)

Publication Number	Publication Date
NL9101623A true NL9101623A (nl)	1993-04-16

Family

ID=19859747

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL9101623A NL9101623A (nl)	1991-09-26	1991-09-26	Werkwijze voor de bereiding van een alcohol.

Country Status (6)

Country	Link
US (1)	US5276190A (de)
EP (1)	EP0534553B1 (de)
JP (1)	JPH05201936A (de)
AT (1)	ATE128456T1 (de)
DE (1)	DE69205107T2 (de)
NL (1)	NL9101623A (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5399763A (en) *	1993-02-01	1995-03-21	Nippon Kayaku Kabushiki Kaisha	Process for preparing optically active 2-aminopropanal
JP3870419B2 (ja) *	1994-08-22	2007-01-17	三菱ウェルファーマ株式会社	ベンゼン化合物およびその医薬としての用途
US5948820A (en)	1994-08-22	1999-09-07	Yoshitomi Pharmaceutical Industries, Ltd.	Benzene compound and pharmaceutical use thereof
RU2330839C2 (ru) *	2002-01-11	2008-08-10	Санкио Компани, Лимитед	Производные аминоспиртов или производные фосфорных кислот и фармацевтические композиции, содержащие указанные производные
TWI355934B (en)	2004-02-24	2012-01-11	Sankyo Co	Pharmaceutical composition for treatment or prophy
CN110054538B (zh) *	2018-01-19	2021-02-09	中国农业大学	一种将叔酰胺还原为胺的方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2618658A (en) *	1949-06-08	1952-11-18	Eastman Kodak Co	2,2-dimethyl-3-hydroxypropylamine and process for its preparation
JPH0653161B2 (ja) *	1988-09-28	1994-07-20	東洋紡績株式会社	循環装置

1991
- 1991-09-26 NL NL9101623A patent/NL9101623A/nl not_active Application Discontinuation
1992
- 1992-09-22 EP EP92202911A patent/EP0534553B1/de not_active Expired - Lifetime
- 1992-09-22 AT AT92202911T patent/ATE128456T1/de not_active IP Right Cessation
- 1992-09-22 JP JP4252676A patent/JPH05201936A/ja active Pending
- 1992-09-22 DE DE69205107T patent/DE69205107T2/de not_active Expired - Fee Related
- 1992-09-25 US US07/950,713 patent/US5276190A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
EP0534553A1 (de)	1993-03-31
ATE128456T1 (de)	1995-10-15
DE69205107T2 (de)	1996-05-09
EP0534553B1 (de)	1995-09-27
JPH05201936A (ja)	1993-08-10
US5276190A (en)	1994-01-04
DE69205107D1 (de)	1995-11-02

Legal Events

Date	Code	Title	Description
1993-04-16	A1B	A search report has been drawn up
1994-05-02	BV	The patent application has lapsed

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