Borane;tetrahydrofuran → (2S)-tert-butyl 4-Hydroxy-2-(hydroxymethyl)piperidine-1-carboxylate

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Reaction Steps

A solution of (S)-1-(tert-butoxycarbonyl)-4-oxopiperidine-2-carboxylic acid (5 g, 20.55 mmol) in tetrahydrofuran (100 mL) under nitrogen was cooled in an ice bath. 1N Borane-tetrahydrofuran in tetrahydrofuran (61.7 mL, 61.7 mmol) was added dropwise over 25 minutes and the mixture was stirred at room temperature for 3 hours, cooled to 0° C. and quenched with 10 mL water. Potassium carbonate (5 g) was added and the mixture was stirred overnight at room temperature, and partitioned between water and ether (three times). The ether extracts were dried over sodium sulfate, filtered, concentrated onto silica gel, and purified by flash chromatography (gradient of 0-100% ethyl acetate-heptanes) to give the title compound as a mixture of diastereomers. MS (ESI+) m/z 231.9 (M+H)+.

Provenance & Evidence