JPH0312055B2 - - Google Patents
Info
- Publication number
- JPH0312055B2 JPH0312055B2 JP22604285A JP22604285A JPH0312055B2 JP H0312055 B2 JPH0312055 B2 JP H0312055B2 JP 22604285 A JP22604285 A JP 22604285A JP 22604285 A JP22604285 A JP 22604285A JP H0312055 B2 JPH0312055 B2 JP H0312055B2
- Authority
- JP
- Japan
- Prior art keywords
- aminopyrrolidine
- water
- added
- benzene
- distilled
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 108
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 36
- NGXSWUFDCSEIOO-UHFFFAOYSA-N pyrrolidin-3-amine Chemical compound NC1CCNC1 NGXSWUFDCSEIOO-UHFFFAOYSA-N 0.000 description 36
- 238000009835 boiling Methods 0.000 description 29
- 239000003054 catalyst Substances 0.000 description 29
- 239000010410 layer Substances 0.000 description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 24
- 239000001257 hydrogen Substances 0.000 description 24
- 229910052739 hydrogen Inorganic materials 0.000 description 24
- 229910052757 nitrogen Inorganic materials 0.000 description 24
- 239000000203 mixture Substances 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 238000003756 stirring Methods 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 235000011121 sodium hydroxide Nutrition 0.000 description 15
- 239000012044 organic layer Substances 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
- BHEXKVGLZMEJRQ-UHFFFAOYSA-N n,1-dibenzylpyrrolidin-3-amine Chemical compound C=1C=CC=CC=1CNC(C1)CCN1CC1=CC=CC=C1 BHEXKVGLZMEJRQ-UHFFFAOYSA-N 0.000 description 13
- 235000013844 butane Nutrition 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 12
- 239000012299 nitrogen atmosphere Substances 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- -1 amino compound Chemical class 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000001273 butane Substances 0.000 description 9
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 9
- SBMSLRMNBSMKQC-UHFFFAOYSA-N pyrrolidin-1-amine Chemical compound NN1CCCC1 SBMSLRMNBSMKQC-UHFFFAOYSA-N 0.000 description 9
- 238000006722 reduction reaction Methods 0.000 description 9
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000012264 purified product Substances 0.000 description 7
- NJPNCMOUEXEGBL-UHFFFAOYSA-N pyrrolidin-1-ium-3-ylazanium;dichloride Chemical compound Cl.Cl.NC1CCNC1 NJPNCMOUEXEGBL-UHFFFAOYSA-N 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000007983 Tris buffer Substances 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 150000003141 primary amines Chemical class 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- UKFHIKGQGFCINK-UHFFFAOYSA-N 1,2,4-tribromobutane Chemical compound BrCCC(Br)CBr UKFHIKGQGFCINK-UHFFFAOYSA-N 0.000 description 3
- PIQHRAXKAGNHCM-UHFFFAOYSA-N 1,2,4-trichlorobutane Chemical compound ClCCC(Cl)CCl PIQHRAXKAGNHCM-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 230000005484 gravity Effects 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
- DAZXKDNMZIGPQQ-UHFFFAOYSA-N 1,2-dibromo-4-chlorobutane Chemical compound ClCCC(Br)CBr DAZXKDNMZIGPQQ-UHFFFAOYSA-N 0.000 description 2
- NBBRIIZFMWSCHJ-UHFFFAOYSA-N 1-benzylpyrrolidin-3-amine;dihydrochloride Chemical compound Cl.Cl.C1C(N)CCN1CC1=CC=CC=C1 NBBRIIZFMWSCHJ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- STQPFXFZBVKNSZ-UHFFFAOYSA-N CC(O)=O.CC(O)=O.NC1CCNC1 Chemical compound CC(O)=O.CC(O)=O.NC1CCNC1 STQPFXFZBVKNSZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical compound C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- MXAQYXXHPDEVDM-UHFFFAOYSA-N pyrrolidin-1-amine;dihydrochloride Chemical compound Cl.Cl.NN1CCCC1 MXAQYXXHPDEVDM-UHFFFAOYSA-N 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 description 1
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
- OHSSXJLLWCUPEV-UHFFFAOYSA-N 4,4-dichlorobutan-1-ol Chemical compound OCCCC(Cl)Cl OHSSXJLLWCUPEV-UHFFFAOYSA-N 0.000 description 1
- DMAYBPBPEUFIHJ-UHFFFAOYSA-N 4-bromobut-1-ene Chemical compound BrCCC=C DMAYBPBPEUFIHJ-UHFFFAOYSA-N 0.000 description 1
- WKEVRZCQFQDCIR-UHFFFAOYSA-N 4-chlorobut-1-ene Chemical compound ClCCC=C WKEVRZCQFQDCIR-UHFFFAOYSA-N 0.000 description 1
- KBPHGYUXEIDPPV-UHFFFAOYSA-N 4-oxo-1h-1,8-naphthyridine-3-carboxylic acid Chemical compound C1=CC=C2C(=O)C(C(=O)O)=CNC2=N1 KBPHGYUXEIDPPV-UHFFFAOYSA-N 0.000 description 1
- 229910020366 ClO 4 Inorganic materials 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000000039 congener Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000006264 debenzylation reaction Methods 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- HDCCJUCOIKLZNM-UHFFFAOYSA-N n-pyrrolidin-3-ylacetamide Chemical compound CC(=O)NC1CCNC1 HDCCJUCOIKLZNM-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 150000004010 onium ions Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- NPPLFOLRHWBLKV-UHFFFAOYSA-N pyrrolidin-3-amine;hydrochloride Chemical compound Cl.NC1CCNC1 NPPLFOLRHWBLKV-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000013077 target material Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyrrole Compounds (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22604285A JPS6287565A (ja) | 1985-10-11 | 1985-10-11 | ３−アミノピロリジンおよびその塩の製造法 |
| US06/916,936 US4785119A (en) | 1985-10-11 | 1986-10-07 | 3-aminopyrrolidine compound and process for preparation thereof |
| DE8686113972T DE3686387T2 (de) | 1985-10-11 | 1986-10-08 | Verfahren zur herstellung von 3-aminopyrrolidine. |
| EP86113972A EP0218249B1 (en) | 1985-10-11 | 1986-10-08 | Process for the production of 3-aminopyrrolidines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22604285A JPS6287565A (ja) | 1985-10-11 | 1985-10-11 | ３−アミノピロリジンおよびその塩の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6287565A JPS6287565A (ja) | 1987-04-22 |
| JPH0312055B2 true JPH0312055B2 (enrdf_load_stackoverflow) | 1991-02-19 |
Family
ID=16838868
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22604285A Granted JPS6287565A (ja) | 1985-10-11 | 1985-10-11 | ３−アミノピロリジンおよびその塩の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6287565A (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04346971A (ja) * | 1991-05-21 | 1992-12-02 | Fujisawa Pharmaceut Co Ltd | ピロリジン化合物またはその塩の製造法 |
| HUE028373T2 (en) | 2004-05-28 | 2017-02-28 | Mitsubishi Tanabe Pharma Corp | Arylalkylamines and processes for their preparation |
-
1985
- 1985-10-11 JP JP22604285A patent/JPS6287565A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6287565A (ja) | 1987-04-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2514935C2 (ru) | Способ получения стимулятора апоптоза авт-263 | |
| JPH0262854A (ja) | 置換フェノキシアセトアルデヒドオキシム類の製造方法 | |
| JPH02218664A (ja) | 光学活性な１ｈ−３−アミノピロリジン化合物の製造法 | |
| JPH0312055B2 (enrdf_load_stackoverflow) | ||
| Decicco et al. | Asymmetric Synthesis of 2, 3-Disubstituted Succinates via Chiral Oxazolidinone Controlled Displacement of. alpha.-Trifluoromethanesulfonate Substituted Esters | |
| US4870189A (en) | Process for synthesis of azetidine and novel intermediates therefor | |
| US3435047A (en) | Process for preparing 3-aminoisoxazole derivatives | |
| JP4270524B2 (ja) | シクロアルキルおよびハロアルキルｏ−アミノフエニルケトン類の改良された製造方法 | |
| EP1002798A1 (en) | An improved process for preparing a therapeutically active pyrazolopyrimidinone derivative | |
| Causey et al. | A Practical Synthesis of Azetidine | |
| US4966979A (en) | Process for synthesis of azetidine and novel intermediates therefor | |
| US4748276A (en) | Process for preparing N,N-bis(2-hydroxyethyl)benzylamine and N,N-bis(2-chloroethyl)benzylamine | |
| JPS6059231B2 (ja) | ピルブテロ−ルおよび同族体の製造のための中間体 | |
| JP2001055360A (ja) | ニトロフェニルフェノール化合物の製造法 | |
| JPH023672A (ja) | ２，６‐ジエチルアニリン誘導体およびその製法 | |
| EP0713865A1 (fr) | Dérivés d'acide 2-aminobenzènesulfonique et de chlorure de 2-aminobenzènesulfonyle, leur préparation et leur utilisation comme intermédiaires de synthèse | |
| US5998614A (en) | Preparation of asymmetric cyclic ureas using an alkali metal in liquid ammonia process | |
| US5220041A (en) | Sulfonate ester | |
| US4806656A (en) | Preparation of N-thienyl-chloroacetamides and tetrahydro-thien-3-ylidenimines | |
| JP3569428B2 (ja) | ホモアリルアミン類の製造方法 | |
| JPH0320391B2 (enrdf_load_stackoverflow) | ||
| US5107026A (en) | Fluorinated acetylene-containing aromatic amines and diamines | |
| JPH01249739A (ja) | オルトー脂肪族オキシフェノール誘導体の製造方法 | |
| JPH0446175A (ja) | ５―ヒドロキシ―３，４―メチレンジオキシ安息香酸誘導体の製造法 | |
| JPS6377844A (ja) | ｐ−ブロモアニリン類の製造法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |