JPS6364435B2 - - Google Patents
Info
- Publication number
- JPS6364435B2 JPS6364435B2 JP54070366A JP7036679A JPS6364435B2 JP S6364435 B2 JPS6364435 B2 JP S6364435B2 JP 54070366 A JP54070366 A JP 54070366A JP 7036679 A JP7036679 A JP 7036679A JP S6364435 B2 JPS6364435 B2 JP S6364435B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- multiplet
- diazabicyclo
- octane
- optically active
- Prior art date
- 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
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)
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)
| Title |
|---|
| CHEMISTRY LETTERS * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55162787A (en) | 1980-12-18 |
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