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

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Reaction Steps

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.

Provenance & Evidence