JPS6364435B2 - - Google Patents

Info

Publication number: JPS6364435B2
Authority: JP; Japan
Prior art keywords: group; multiplet; diazabicyclo; octane; optically active
Prior art date: 1979-06-04
Legal status (The legal status 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 status listed.): Expired

Application number

JP54070366A

Other languages

English (en)

Japanese (ja)

Other versions

JPS55162787A (en

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.)

1979-06-04

Filing date

1979-06-04

Publication date

1988-12-12

1979-06-04 Application filed filed Critical

1979-06-04 Priority to JP7036679A priority Critical patent/JPS55162787A/ja

1979-10-30 Priority to US06/089,356 priority patent/US4337346A/en

1979-11-02 Priority to DE8181108506T priority patent/DE2967419D1/de

1979-11-02 Priority to EP81108507A priority patent/EP0048501B1/en

1979-11-02 Priority to DE7979302419T priority patent/DE2965322D1/de

1979-11-02 Priority to DE8181108507T priority patent/DE2966001D1/de

1979-11-02 Priority to EP81108506A priority patent/EP0050351B1/en

1979-11-02 Priority to EP79302419A priority patent/EP0011417B1/en

1980-12-18 Publication of JPS55162787A publication Critical patent/JPS55162787A/ja

1981-04-27 Priority to US06/257,587 priority patent/US4383122A/en

1983-01-13 Priority to US06/457,666 priority patent/US4584387A/en

1988-12-12 Publication of JPS6364435B2 publication Critical patent/JPS6364435B2/ja

Status Granted legal-status Critical Current

Links

150000004795 grignard reagents Chemical class 0.000 claims description 11
-1 magnesium halide Chemical class 0.000 claims description 11
239000007818 Grignard reagent Substances 0.000 claims description 10
150000007854 aminals Chemical class 0.000 claims description 10
125000003118 aryl group Chemical group 0.000 claims description 9
HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical class OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
239000011777 magnesium Substances 0.000 claims description 6
229910052749 magnesium Inorganic materials 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
239000000203 mixture Substances 0.000 description 12
239000000243 solution Substances 0.000 description 12
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 8
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
238000010992 reflux Methods 0.000 description 7
239000002904 solvent Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
235000019270 ammonium chloride Nutrition 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
IVRYBIASBRGJQI-UHFFFAOYSA-N methyl 2-phenyl-1,3,5,6,7,7a-hexahydropyrrolo[1,2-c]imidazole-3-carboxylate Chemical compound COC(=O)C1N2CCCC2CN1C1=CC=CC=C1 IVRYBIASBRGJQI-UHFFFAOYSA-N 0.000 description 3
MCHWKJRTMPIHRA-NSHDSACASA-N n-[[(2s)-pyrrolidin-2-yl]methyl]aniline Chemical compound C([C@H]1NCCC1)NC1=CC=CC=C1 MCHWKJRTMPIHRA-NSHDSACASA-N 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
IBLCBXMDPIZZOB-UHFFFAOYSA-N 2,3,3a,4,5,6-hexahydro-1h-pyrrolo[1,2-b]pyrazole Chemical compound C1CNN2CCCC21 IBLCBXMDPIZZOB-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical class O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
229910001629 magnesium chloride Inorganic materials 0.000 description 2
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
DJSCQCGHDWBAMG-VIFPVBQESA-N (2r)-2-hydroxy-2-phenylpropanal Chemical compound O=C[C@@](O)(C)C1=CC=CC=C1 DJSCQCGHDWBAMG-VIFPVBQESA-N 0.000 description 1
BEYTUOFWMWNNTA-UHFFFAOYSA-N 1-(2-phenyl-1,3,5,6,7,7a-hexahydropyrrolo[1,2-c]imidazol-3-yl)ethanone Chemical compound CC(=O)C1N2CCCC2CN1C1=CC=CC=C1 BEYTUOFWMWNNTA-UHFFFAOYSA-N 0.000 description 1
NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical class C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
HTGNDXZAOJQEQK-UHFFFAOYSA-N 2-methyl-1-(2-phenyl-1,3,5,6,7,7a-hexahydropyrrolo[1,2-c]imidazol-3-yl)propan-1-one Chemical compound CC(C)C(=O)C1N2CCCC2CN1C1=CC=CC=C1 HTGNDXZAOJQEQK-UHFFFAOYSA-N 0.000 description 1
125000006024 2-pentenyl group Chemical group 0.000 description 1
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
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
125000006058 4-methyl-4-pentenyl group Chemical group 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
238000003747 Grignard reaction Methods 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
150000004791 alkyl magnesium halides Chemical class 0.000 description 1
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004792 aryl magnesium halides Chemical class 0.000 description 1
FWTXWYXPXGKVJG-UHFFFAOYSA-N atrolactamide Chemical compound NC(=O)C(O)(C)C1=CC=CC=C1 FWTXWYXPXGKVJG-UHFFFAOYSA-N 0.000 description 1
229950011225 atrolactamide Drugs 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
238000009835 boiling Methods 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000012973 diazabicyclooctane Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
XNLXZJSWGZWDMZ-UHFFFAOYSA-N ethyl 2-phenyl-1,3,5,6,7,7a-hexahydropyrrolo[1,2-c]imidazole-3-carboxylate Chemical compound CCOC(=O)C1N2CCCC2CN1C1=CC=CC=C1 XNLXZJSWGZWDMZ-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
229940015043 glyoxal Drugs 0.000 description 1
230000003301 hydrolyzing effect Effects 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
OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
229910001623 magnesium bromide Inorganic materials 0.000 description 1
BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 description 1
229910001641 magnesium iodide Inorganic materials 0.000 description 1
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
LVKCSZQWLOVUGB-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].C[CH-]C LVKCSZQWLOVUGB-UHFFFAOYSA-M 0.000 description 1
RNVVYVPDHMKDTL-UHFFFAOYSA-N methyl 2-(hydroxymethoxy)acetate Chemical compound COC(=O)COCO RNVVYVPDHMKDTL-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000010446 mirabilite Substances 0.000 description 1
239000012046 mixed solvent Substances 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
125000001624 naphthyl group Chemical group 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
XYUQMENHCBNLPM-UHFFFAOYSA-N phenyl-(2-phenyl-1,3,5,6,7,7a-hexahydropyrrolo[1,2-c]imidazol-3-yl)methanone Chemical compound C=1C=CC=CC=1C(=O)C1N2CCCC2CN1C1=CC=CC=C1 XYUQMENHCBNLPM-UHFFFAOYSA-N 0.000 description 1
125000004344 phenylpropyl group Chemical group 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Landscapes

Nitrogen Condensed Heterocyclic Rings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP7036679A 1978-11-02 1979-06-04 Aminal derivative and its preparation Granted JPS55162787A (en)

Priority Applications (10)

Application Number	Priority Date	Filing Date	Title
JP7036679A JPS55162787A (en)	1979-06-04	1979-06-04	Aminal derivative and its preparation
US06/089,356 US4337346A (en)	1978-11-02	1979-10-30	α-Hydroxyaldehyde and a process for preparing the same
DE8181108507T DE2966001D1 (en)	1978-11-02	1979-11-02	Optically active or racemic diazabicyclooctane derivatives
EP81108507A EP0048501B1 (en)	1978-11-02	1979-11-02	Optically active or racemic diazabicyclooctane derivatives
DE7979302419T DE2965322D1 (en)	1978-11-02	1979-11-02	Optically active or racemic aminal derivatives, process for preparing same and for converting same to alpha-hydroxyaldehydes
DE8181108506T DE2967419D1 (en)	1978-11-02	1979-11-02	Optically active or racemic alpha-hydroxyaldehydes and benzyl derivatives thereof
EP81108506A EP0050351B1 (en)	1978-11-02	1979-11-02	Optically active or racemic alpha-hydroxyaldehydes and benzyl derivatives thereof
EP79302419A EP0011417B1 (en)	1978-11-02	1979-11-02	Optically active or racemic aminal derivatives, process for preparing same and for converting same to alpha-hydroxyaldehydes
US06/257,587 US4383122A (en)	1978-11-02	1981-04-27	Process for preparing α-hydroxyaldehyde
US06/457,666 US4584387A (en)	1978-11-02	1983-01-13	Acyl and ester derivatives of 1,3-diazabicyclo[3,3,0]octane

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP7036679A JPS55162787A (en)	1979-06-04	1979-06-04	Aminal derivative and its preparation

Publications (2)

Publication Number	Publication Date
JPS55162787A JPS55162787A (en)	1980-12-18
JPS6364435B2 true JPS6364435B2 (da)	1988-12-12

Family

ID=13429360

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP7036679A Granted JPS55162787A (en)	1978-11-02	1979-06-04	Aminal derivative and its preparation

Country Status (1)

Country	Link
JP (1)	JPS55162787A (da)

1979
- 1979-06-04 JP JP7036679A patent/JPS55162787A/ja active Granted

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMISTRY LETTERS *

Also Published As

Publication number	Publication date
JPS55162787A (en)	1980-12-18

Publication	Publication Date	Title
EP0050351B1 (en)	1985-03-27	Optically active or racemic alpha-hydroxyaldehydes and benzyl derivatives thereof
Plé et al.	1997	Synthesis and metalation of trifluoromethylpyrimidines. Metalation of diazines. XVI
JPS6364435B2 (da)	1988-12-12
JPS6148488B2 (da)	1986-10-24
JPS62201842A (ja)	1987-09-05	３−ヒドロキシシクロペント−４−エン−１−オン類の製造法
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SU523100A1 (ru)	1976-07-30	"Способ получени (бромметил)или (иодметил)-трихлорсиланов
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JPH07126217A (ja)	1995-05-16	５−ヒドロキシ−３−ケトエステル誘導体の製造方法