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

HRID 20333

반응식

HRID 20333 반응식
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C@@H:13]([OH:27])[C@@H:14]([N+:24]([O-])=O)[CH2:15][C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[C:18]([F:23])[CH:17]=2)[CH2:11][O:10][C:9]1([CH3:29])[CH3:28])=[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:12]([C@@H:13]([OH:27])[C@@H:14]([NH2:24])[CH2:15][C:16]2[CH:17]=[C:18]([F:23])[CH:19]=[C:20]([F:22])[CH:21]=2)[CH2:11][O:10][C:9]1([CH3:29])[CH3:28])=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 58972248(R)-4-[(1R,2S)-3-(3,5-difluorophenyl)-1-hydroxy-2-nitropropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

생성물 1

HCID 68562294(R)-4-[(1S,2S)-2-Amino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester수율 95%

시약·촉매·용매 2

HCID 24385Nickel Dichloride촉매HCID 887Methanol용매

실험 절차

Combine (R)-4-[(1R,2S)-3-(3,5-difluorophenyl)-1-hydroxy-2-nitropropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (1.13 g, 2.71 mmol) and nickel (II) chloride (0.58 g, 4.485 mmol) in dry methanol (30 ml) and add sodium borohydride (0.454 g, 12 mmol) over 1 minute. Stir the resulting mixture for 20 minutes and then add water (3 mL). Concentrate and dissolve the residue in ethyl acetate. Filter the black solution through a pad of Celite® and wash the filter cake with ethyl acetate. Wash the filtrate with water (twice), saturated aqueous sodium chloride, dry (magnesium sulfate), filter, and concentrate to give the desired compound as a white solid (920 mg, 95%).

후처리

  1. concentrationConcentrate
  2. dissolutiondissolve the residue in ethyl acetate
  3. filtrationFilter the black solution through a pad of Celite®
  4. washwash the filter cake with ethyl acetate
  5. washWash the filtrate with water (twice), saturated aqueous sodium chloride
  6. dry with materialdry (magnesium sulfate)
  7. filtrationfilter
  8. concentrationconcentrate

출처 및 근거

ORD 기록
ord-cc02d55a1a304c93a1f76ea81947d101
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745438B2

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