Sodium borohydride → 4-(R)-[2-(S)-Amino-1-(S)-hydroxy-3-(3-hydroxyphenyl)-propyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

HRID 20348

반응식

HRID 20348 반응식
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C@@H:13]([OH:29])[C@@H:14]([N+:26]([O-])=O)[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22]C(=O)C)[CH:17]=2)[CH2:11][O:10][C:9]1([CH3:31])[CH3:30])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO.[Ni](Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C@@H:13]([OH:29])[C@@H:14]([NH2:26])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=2)[CH2:11][O:10][C:9]1([CH3:31])[CH3:30])=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 2

HCID 4311764Sodium borohydrideHCID 685609864-(R)-[3-(3-Acetoxyphenyl)-1-(R)-hydroxy-2-(S)-nitropropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

생성물 1

HCID 685597324-(R)-[2-(S)-Amino-1-(S)-hydroxy-3-(3-hydroxyphenyl)-propyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

시약·촉매·용매 2

HCID 24385Nickel Dichloride촉매HCID 887Methanol용매

실험 절차

Add nickel (II) chloride (6.0 g, 46.1 mmol) to a solution of 4-(R)-[3-(3-acetoxyphenyl)-1-(R)-hydroxy-2-(S)-nitropropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (18.37 g, 41.9 mmol) in dry methanol (900 mL). Cool in an ice bath and portionwise sodium borohydride (6.34 g, 167.6 mmol) over 8 minutes. Stir for 10 minutes. And concentrate. Partition the residue between ethyl acetate (200 mL) and water (200 mL), filter through Celite® and wash with ethyl acetate. Wash the organic layer with saturated aqueous sodium chloride, combine aqueous washes and extract with ethyl acetate. Combine the organic layers, dry (magnesium sulfate), filter and concentrate to give the desired compound as a crude foam. Suspend the Celite® cake in ethyl acetate, filter, wash with saturated aqueous sodium chloride, dry (magnesium sulfate), filter and concentrate to obtain more desired compound.

후처리

  1. temperatureCool in an ice bath
  2. concentrationAnd concentrate
  3. customPartition the residue between ethyl acetate (200 mL) and water (200 mL)
  4. filtrationfilter through Celite®
  5. washwash with ethyl acetate
  6. washWash the organic layer with saturated aqueous sodium chloride
  7. extractionextract with ethyl acetate
  8. dry with materialdry (magnesium sulfate)
  9. filtrationfilter
  10. concentrationconcentrate

출처 및 근거

ORD 기록
ord-a887d5da444d4d0aae8eef16fd369179
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745438B2

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