Sodium borohydride → rac-tert-butyl (3R,4R)-3-fluoro-4-hydroxypiperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Sodium borohydride (1.53 g, 40.5 mmol) was added to a stirred solution of tert-butyl 3-fluoro-4-oxopiperidine-1-carboxylate (OmegaChem, 8 g, 36.8 mmol) in dry methanol (100 mL) maintained at 0° C. The reaction mixture was stirred at same temperature for 45 min, it was then quenched with dry acetone (20 mL) and evaporated under reduced pressure. The residue was diluted with EtOAc and washed with water and brine. It was dried over sodium sulfate, filtered and concentrated. Purification by flash chromatography on silica (Pet. Ether: EtOAc, 80:20) afforded the titled compound as white solid (4.0 g, 50%). 1H NMR (400 MHz, DMSO-d6) δ 4.61 (ddd, J=39, 8.6, 3.2 Hz, 1H), 3.93 (m, 2H), 3.71 (bs, 1H), 3.42 (brs, 1H), 3.06-3.00 (m, 1H), 1.88-1.83 (m, 2H), 1.45 (s, 9H). HPLC (Condition A): Rt 2.7 min (purity 97%).

Provenance & Evidence