Ethanol → Benzyl [2-(tert-butyldimethylsilyloxy)-4-hydroxy-1,3,3-trimethylbutyl]carbamate

HRID 906976노트

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HRID 906976 반응식
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH3:30])[CH:13]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[C:14]([CH3:21])([CH3:20])[C:15](OCC)=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Ca+2].[Cl-].C(O)C.[BH4-].[Na+]>C1COCC1.O>[Si:23]([O:22][CH:13]([C:14]([CH3:20])([CH3:21])[CH2:15][OH:16])[CH:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH3:30])([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]

참가 물질

7

반응물 4

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 59556980Ethyl 4-{[(benzyloxy)carbonyl]amino}-2,2-dimethyl-3-(tert-butyldimethylsilyloxy)pentanoate

생성물 1

HCID 59273056Benzyl [2-(tert-butyldimethylsilyloxy)-4-hydroxy-1,3,3-trimethylbutyl]carbamate수율 28.2%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a mixed solution of ethyl 4-{[(benzyloxy)carbonyl]amino}-2,2-dimethyl-3-(tert-butyldimethylsilyloxy)pentanoate (5.42 g) and calcium chloride (2.06 g) in THF (50 mL)-ethanol (25 mL) was added sodium borohydride (1.56 g) and the mixture was stirred at room temperature for 13 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→1/1) to give the title compound as a colorless solid (yield: 1.38 g, yield: 28%).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→1/1)

출처 및 근거

ORD 기록
ord-bf17e195bc364db9bea0510bcdfddbd5
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08013008B2

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