Lithium Hydroxide → HCID 89315948, compound

Participants

Reaction Steps

A mixture of (3aS,4S,5R,6R,7aS)-4-fluoro-5-hydroxy-6-(hydroxymethyl)hexahydrobenzo[d]oxazol-2(3H)-one (704 mg, 3.43 mmol) and LiOH (2.71 g, 113 mmol) in water (35 mL) and MeOH (26 mL) was stirred at reflux for 2 h. The solvents were evaporated to give the crude product. This was purified by SiO2 column, eluted with 20%-30% 2 M NH3 MeOH solution in DCM give (1S,2S,3S,4R,5R)-2-amino-3-fluoro-5-(hydroxymethyl)cyclohexane-1,4-diol (485 mg, 80%) as a white solid. 1H NMR (400 MHz, MeOD) δ 4.74 (d, J=52.0 Hz, 1H), 3.96-3.99 (m, 1H), 3.65-3.73 (m, 2H), 3.49 (ddd, J=28.0 Hz, 10.5 Hz, 1.6 Hz, 1H), 3.05 (d, J=31.0 Hz, 1H), 2.09-2.19 (m, 1H), 1.96 (dt, J=14.5 Hz, 3.7 Hz, 1H), 1.46-1.53 (m, 1H).

Provenance & Evidence