Sodium Hydroxide → HCID 67480625, compound

Participants

Reaction Steps

To a mixture of rac-(3 aS,4R,5R,6R,7aS)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-hexahydrobenzo[d]oxazol-2(3H)-one (280 mg, 0.592 mmol) in ethanol (2 mL) was added 2 N NaOH (10 mL). The mixture was heated at reflux for 16 h. After cooling to room temperature, the mixture was extracted with DCM (3×15 mL). The combined extracts were washed with brine and dried over Na2SO4. Solvents were evaporated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with 5% MeOH in DCM and 94:4:2 DCM-MeOH—NH4OH (28% aqueous) to give rac-(1R,2R,3S,4S,5S)-2-amino-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)cyclohexanol (Intermediate Example 2) (227 mg, 86%) as a white solid. 1H NMR (500 MHz, CDCl3) δ 7.37-7.25 (m, 15H), 5.01 (d, J=11.5 Hz, 1H), 4.84 (d, J=10.9 Hz, 1H), 4.63 (d, J=11.5 Hz, 1H), 4.60 (d, J=10.9 Hz, 1H), 4.47 (s, 2H), 3.86 (q, J=2.8 Hz, 1H), 3.79 (dd, J=9.0, 4.2 Hz, 1H), 3.58-3.53 (m, 2H), 3.44 (dd, J=9.0, 2.5 Hz, 1H), 2.85 (d, J=6.7 Hz, 1H), 2.27-2.15 (m, 1H), 1.94 (dt, J=14.5, 3.5 Hz, 1H), 1.67 (ddd, J=14.8, 12.6 Hz, 2.4, 1H).

Provenance & Evidence