Acetic Acid → Ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-hydroxybutyrate

HRID 280971노트

반응식

HRID 280971 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][C:19](=[O:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.C(O)C.C([BH3-])#N.[Na+]>O>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH:19]([OH:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 702EthanolHCID 5003444Sodium cyanoborohydrideHCID 19868897Ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-oxobutyrate

생성물 1

HCID 20143718Ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-hydroxybutyrate수율 67.3%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a stirred mixture of ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-oxobutyrate (17 g), acetic acid (4.5 g) and ethanol (30 ml) is added sodium cyanoborohydride (3 g) at room temperature. After stirring for 3 hours at room temperature, the mixture is diluted with water (500 ml) and extracted with methylene chloride. The organic extract is dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue is purified by silica gel column chromatography using hexane-ethyl acetate (2:1-1:1) as an eluent to give ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-hydroxybutyrate (11.5 g) as a colorless oil.

후처리

  1. extractionextracted with methylene chloride
  2. extractionThe organic extract
  3. dry with materialis dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-091866747c6844f5a619ab91a57931bd
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04591458

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