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

HRID 376252

反応式

HRID 376252 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d075277b233c45d7906be90b26a3d538
出典データセット
uspto-grants-2000_02
特許番号
US06020336

関連ノート

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