Toluene → (2S,4R)-1-(3-pyridylmethyl)-2-formyl-4-(4-chlorophenylsulfonylamino)pyrrolidine
반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][N:8]2[CH2:12][C@H:11]([NH:13][S:14]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH2:10][C@H:9]2[C:24](OC)=[O:25])[CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][N:8]2[CH2:12][C@H:11]([NH:13][S:14]([C:17]3[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=3)(=[O:15])=[O:16])[CH2:10][C@H:9]2[CH:24]=[O:25])[CH:2]=1참가 물질
반응물 4
생성물 1
시약·촉매·용매 1
반응 조건
- 온도
- -50 °C
실험 절차
In an atmosphere of nitrogen, (2S,4R)-1-(3-pyridylmethyl)-2-methoxycarbonyl-4-(4chlorophenylsulfonylamino)pyrrolidine (10 g, 0.0244 mol) was dissolved in methylene chloride (200 ml) and the solution was cooled to -50°~-55° C. Then, 1M diisobutylaluminum hydride in toluene (73.2 ml, 0.0732 mol) was added thereto dropwise at -50° C. and the mixture was stirred for 30 minutes. Then, 20% sodium potassium tartrate solution was added thereto at 25° C. for precipitation of insolubles. The insolubles were separated by filtration and washed with methylene chloride. The mother liquor and the washings were combined and, after phase separation, the methylene chloride layer was taken. The methylene chloride layer was concentrated to dryness to provide (2S,4R)-1-(3-pyridylmethyl)-2-formyl-4-(4-chlorophenylsulfonylamino)-pyrrolidine (10.4 g) as an oil.
후처리
- temperaturethe solution was cooled to -50°~-55° C
- customat 25° C. for precipitation of insolubles
- customThe insolubles were separated by filtration
- washwashed with methylene chloride
- customafter phase separation
- concentrationThe methylene chloride layer was concentrated to dryness
출처 및 근거
- ORD 기록
- ord-a114289e3237442797c113e8718137a4
- 출처 데이터셋
- uspto-grants-1996_08
- 특허 번호
- US05543525
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