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

HRID 280978Notes

Reaction equation

HRID 280978 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)C.C(O)(=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][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 702EthanolHCID 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 962WaterSolvent

Procedure

To a chilled mixture of ethyl 6-(1-benzyloxycarbonyl-4-piperidyl)-2-oxohexanoate (26 g), ethanol (40 ml) and acetic acid (6.2 g) is added sodium cyanoborohydride (4.4 g) with stirring. After being stirred for 1 hour, the mixture is allowed to stand overnight at room temperature, diluted with water (500 ml) and extracted with methylene chloride. The 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) as an eluent to yield ethyl 6-(1-benzyloxycarbonyl-4-piperidyl)-2-hydroxyhexanoate (16 g) as a colorless oil.

Workup

  1. stirringAfter being stirred for 1 hour
  2. extractionextracted with methylene chloride
  3. dry with materialThe extract is dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-33a609acb27b41428564dcd3d335ef85
Source dataset
uspto-grants-1986_05
Patent number
US04591458

Reaction notes

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