Acetic Acid → 1-(N-tert-butyloxycarbonyl-pyrrolidin-3-ylmethyl)-6-nitro-2,3-dihydroindole

HRID 1003267

반응식

HRID 1003267 반응식
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:15]([O:19][C:20]([N:22]1[CH2:26][CH2:25][CH:24]([CH:27]=O)[CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].[N+:29]([C:32]1[CH:40]=[C:39]2[C:35]([CH2:36][CH2:37][NH:38]2)=[CH:34][CH:33]=1)([O-:31])=[O:30].C(O)(=O)C>ClCCl.C(OCC)(=O)C>[C:15]([O:19][C:20]([N:22]1[CH2:26][CH2:25][CH:24]([CH2:27][N:38]2[C:39]3[C:35](=[CH:34][CH:33]=[C:32]([N+:29]([O-:31])=[O:30])[CH:40]=3)[CH2:36][CH2:37]2)[CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 297576-NitroindolineHCID 4692112(+-)-1-(tert-Butoxycarbonyl)pyrrolidine-3-carboxaldehydeHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 109369451-(N-tert-butyloxycarbonyl-pyrrolidin-3-ylmethyl)-6-nitro-2,3-dihydroindole

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

91.5 mmol (19.4 g) of solid sodium triacetoxyborohydride are added slowly, at 20° C., to a solution of 60.8 mmol (12.1 g) of 1-(tert-butyloxycarbonyl)-3-formylpyrrolidine, 60.8 mmol (10 g) of 6-nitroindoline and 60.8 mmol (3.65 g) of acetic acid in 100 ml of dichloromethane. After 2 hours stirring, the reaction mixture is diluted with ethyl acetate. The organic phase is washed with water until pH=8, and the aqueous phase is then extracted with dichloromethane. After removal of the solvent by evaporation, the expected product is obtained.

후처리

  1. washThe organic phase is washed with water until pH=8
  2. extractionthe aqueous phase is then extracted with dichloromethane
  3. customAfter removal of the solvent
  4. customby evaporation

출처 및 근거

ORD 기록
ord-b4567f2b5794475f9fcd02f8a86e6d4e
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06046205

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