Borane;tetrahydrofuran → (2S,3R)-benzyl 2-(hydroxymethyl)-3-methylpiperidine-1-carboxylate

Participants

Reaction Steps

To a stirred solution of (−)-(2S,3R)-1-((benzyloxy)carbonyl)-3-methylpiperidine-2-carboxylic acid (6.05 g, 21.8 mmol) in anhydrous THF (80 mL) was added BH3.THF (1 M in THF, 43.6 mL, 43.6 mmol) dropwise over 10 min at rt under nitrogen. The reaction mixture was then stirred at rt for 46 h. After this time, the reaction was quenched by the slow addition of ice cold water (10 mL) followed by 2 N HCl (20 mL). The resulting mixture was stirred at rt for 30 min and then extracted with EtOAc (3×100 mL). The combined extracts were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel eluting with 20% to 50% EtOAc/CH2Cl2 to afford the title compound as a colorless oil (5.30 g, 92%). ESI MS (M+H) 264.

Provenance & Evidence