Acetic Acid → Ethyl 6-(1-benzyloxycarbonyl-4-piperidyl)-2-hydroxyhexanoate

HRID 980609Notes

Reaction equation

HRID 980609 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][C:21](=[O:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[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][CH2:19][CH2:20][CH:21]([OH:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[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 13817563Ethyl 6-(1-benzyloxycarbonyl-4-piperidyl)-2-oxohexanoate

Product 1

HCID 13817553Ethyl 6-(1-benzyloxycarbonyl-4-piperidyl)-2-hydroxyhexanoateYield 61.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 40 ml of ethanol is dissolved 26 g of ethyl 6-(1-benzyloxycarbonyl-4-piperidyl)-2-oxohexanoate, and 6.2 g of acetic acid is added to the solution. Sodium cyanoborohydride (4.4 g) is added to the mixture under ice-cooling, and the mixture is stirred for 1 hour and allowed to stand at room temperature overnight. Water (500 ml) is added to the reaction solution, followed by extraction with methylene chloride. The extract is dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting brown viscous material is purified by silica-gel column chromatography (hexane:ethyl acetate=2:1) to give 16 g of ethyl 6-(1-benzyloxycarbonyl-4-piperidyl)-2-hydroxyhexanoate as a colorless oily material.

Workup

  1. additionis added to the solution
  2. temperaturecooling
  3. waitto stand at room temperature overnight
  4. extractionfollowed by extraction with methylene chloride
  5. dry with materialThe extract is dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting brown viscous material is purified by silica-gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-8431c85dddc14ee880a77e38f3e9dc6c
Source dataset
uspto-grants-1987_01
Patent number
US04638000

Reaction notes

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