Lithium Hydroxide → HCID 117856476, compound

Participants

Reaction Steps

To a solution of (3aR,4R,5R,6S,7aS)-6-(difluoromethyl)-4,5-dihydroxyhexahydrobenzo[d]oxazol-2(3H)-one (255 mg, 1.48 mmol) in MeOH (2 mL) and water (3 mL) was added LiOH (600 mg, 25.0 mmol). The mixture was heated at reflux for 2 h. Solvents were evaporated and the residue was purified by silica gel column chromatography, eluted with 20% 2 M NH3 MeOH solution in DCM to give the product (1R,2R,3S,4S,6S)-3-amino-6-(difluoromethyl)cyclohexane-1,2,4-triol (214 mg, 99%) as a white solid. MS m/z 198.1 (M+1, 100%); 1H NMR (400 MHz, MeOD) δ 6.14 (t, J=57.2 Hz, 1H), 4.15 (br s, 1H), 3.63 (t, J=9.7 Hz, 1H), 3.30 (t, J=11.0 Hz, 1H), 2.91 (dd, J=10.4 Hz, 2.8 Hz, 1H), 2.20-2.36 (m, 1H), 1.97 (dt, J=14.4 Hz, 3.6 Hz, 1H), 1.53-1.60 (m, 1H).

Provenance & Evidence