HCID 71152401, compound → HCID 117857041, compound

Participants

Reaction Steps

A mixture of (3aS,4R,5R,6S,7aS)-4,5-bis(benzyloxy)-6-(fluoromethyl)hexahydrobenzo[d]oxazol-2(3H)-one (410 mg, 1.065 mmol) in ethanol (8 mL), water (8 mL) and 5 N NaOH (4 mL) was heated at reflux for 2 h. After cooling, the reaction was diluted with water (50 mL), extracted with DCM (3×25 mL) and dried with Na2SO4. The solvent was evaporated to give (1S,2S,3R,4R,5S)-2-amino-3,4-bis(benzyloxy)-5-(fluoromethyl)cyclohexanol as a white solid (370 mg, 97%) which was pure enough for next reaction. MS m/z 382.2 (M+23, 100%); 1H NMR (400 MHz, CDCl3) δ 7.29-7.39 (m, 10H), 5.03 (d, J=11.4 Hz, 1H), 4.91 (d, J=10.9 Hz, 1H), 4.78 (ddd, J=48.0 Hz, 9.0 Hz, 3.0 Hz, 1H), 4.67 (d, J=10.9 Hz, 1H), 4.65 (d, J=11.4 Hz, 1H), 4.37 (ddd, J=47.4 Hz, 9.1 Hz, 2.0 Hz, 1H), 3.88 (br s, 1H), 3.58 (t, J=9.4 Hz, 1H), 3.48 (t, J=9.9 Hz, 1H), 2.11-2.26 (m, 1H), 1.95 (dt, J=14.3 Hz, 3.1 Hz, 1H), 1.63 (t, J=13.6 Hz, 1H).

Provenance & Evidence