Water → (R)-5-[(1S,2S)-2-Amino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2,2-diphenylmorpholine-4-carboxylic acid tert-butyl ester

HRID 20398

反応式

HRID 20398 の反応式
[C:1]([O:5][C:6]([N:8]1[C@@H:13]([C@@H:14]([OH:28])[C@@H:15]([N+:25]([O-])=O)[CH2:16][C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[CH:18]=2)[CH2:12][O:11][C:10]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].O>CO.[Ni](Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C@@H:13]([C@@H:14]([OH:28])[C@@H:15]([NH2:25])[CH2:16][C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[CH:18]=2)[CH2:12][O:11][C:10]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 68563474(R)-5-[(1R,2S)-3-(3,5-difluorophenyl)-1-hydroxy-2-nitropropyl]-2,2-diphenylmorpholine-4-carboxylic acid tert-butyl ester

生成物 1

HCID 68561345(R)-5-[(1S,2S)-2-Amino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2,2-diphenylmorpholine-4-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 24385Nickel Dichloride触媒HCID 887Methanol溶媒

実験手順

Dissolve (R)-5-[(1R,2S)-3-(3,5-difluorophenyl)-1-hydroxy-2-nitropropyl]-2,2-diphenylmorpholine-4-carboxylic acid tert-butyl ester (0.172 g, 0.31 mmol) in dry methanol (8 mL), add nickel chloride (0.060 g, 0.46 mmol) then sodium borohydride (0.059 g, 1.55 mmol). Stir 15 minutes, add water (˜2 mL) and concentrate. Add ethyl acetate (˜70 mL), filter (Celite®), wash with water and saturated aqueous sodium chloride. Dry (magnesium sulfate), filter and concentrate to give the desired compound as a white solid.

後処理

  1. concentrationconcentrate
  2. filtrationAdd ethyl acetate (˜70 mL), filter (Celite®)
  3. washwash with water and saturated aqueous sodium chloride
  4. dry with materialDry (magnesium sulfate)
  5. filtrationfilter
  6. concentrationconcentrate

出典と根拠

ORDレコード
ord-3e2bffbbd863498888e852199d458adc
出典データセット
uspto-grants-2010_06
特許番号
US07745438B2

関連ノート

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