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

HRID 649394ノート

反応式

HRID 649394 の反応式
[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([BH3-])#N.[Na+].O>C(O)C>[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

参加物

6

反応物 4

HCID 176Acetic AcidHCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 19868897Ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-oxobutyrate

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

In 30 ml of ethanol is dissolved 17 g of ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-oxobutyrate, and 4.5 g of acetic acid is added to the solution. Sodium cyanoborohydride (3 g) is added to the mixture at room temperature with stirring, followed by stirring at room temperature for 3 hours, and 500 ml of water is added to the reaction mixture, which is extracted with methylene chloride. The extract is dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the resulting residue is purified by silica-gel column chromatography (hexane:ethyl acetate=2:1 to 1:1) to give 11.5 g of ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-hydroxybutyrate as a colorless oily material.

後処理

  1. additionis added to the solution
  2. stirringby stirring at room temperature for 3 hours
  3. extractionis extracted with methylene chloride
  4. dry with materialThe extract is dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe resulting residue is purified by silica-gel column chromatography (hexane:ethyl acetate=2:1 to 1:1)

出典と根拠

ORDレコード
ord-200718cb94214930967b313c6ce8dc68
出典データセット
uspto-grants-1988_04
特許番号
US04739066

反応ノート

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