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

HRID 980604Notes

Reaction equation

HRID 980604 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-dda132f23b6c484499db454e585b69f6
Source dataset
uspto-grants-1987_01
Patent number
US04638000

Reaction notes

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