Water → phenylmethyl (2S)-2-(hydroxymethyl)-1-piperidinecarboxylate

Participants

Reaction Steps

(2S)-1-{[(Phenylmethyl)oxy]carbonyl}-2-piperidinecarboxylic acid (1.0 g, 3.798 mmol) in THF (5 mL) was cooled to −18° C. and borane-THF complex (3.798 mL, 3.798 mmol) was added over 10 min. The mixture was allowed to warm to room temperature with stirring overnight, then cooled to 0° C., and water (4 mL) was added, followed by K2CO3 (1.4 g). The phases were separated, and the aqueous phase was extracted with Et2O (3×25 mL). The combined organic phase was washed with brine (1×25 mL) and dried over anhydrous MgSO4, filtered, and concentrated in vacuo to provide phenylmethyl (2S)-2-(hydroxymethyl)-1-piperidinecarboxylate (815 mg, 86%). LCMS: (M+H)+: 250.2.

Provenance & Evidence