Water → 1-Benzyl-4-(hydroxymethyl)piperidin-3-ol

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Reaction Steps

Sodium borohydride (40 g) was added in portions to a stirred solution of ethyl N-benzyl-3-oxopiperidine-4-carboxylate hydrochloride (23.6 g, 90 mmol) in methanol (500 mL), over 2 h. Water (300 mL) was added slowly, the mixture stirred for 15 min and then the organics were evaporated. The residue was partitioned between DCM and water (×3), the combined organic layers dried over anhydrous sodium sulfate, and the solvent evaporated to give 1-benzyl-4-hydroxymethyl-piperidin-3-ol product as a cis/trans mixture, which was used in the next step without further purification. M.S (M+1): 222.

Provenance & Evidence