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

HRID 20333
ノート
印刷プレビュー

反応式

HRID 20333 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24385
Nickel Dichloride
触媒
HCID 887Methanol溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-cc02d55a1a304c93a1f76ea81947d101
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07745438B2

反応ノート

読み込み中…

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