Acetic Acid → HCID 86596967, compound

Participants

Reaction Steps

A solution of acetic acid, water, and THF (30 mL, 3:1:1) was added to benzyl (1S,2R)-2-((tert-butyldimethylsilyloxy)methyl)-4-oxocyclohexylcarbamate (2.56 g) in one portion. After 48 h, the reaction solvent was removed in vacuo and replaced with ethyl acetate (100 mL). The mixture was washed with water (1×25 mL), sat'd NaHCO3 (2×25 mL), and brine (1×25 mL). The resulting organic layer was dried over MgSO4, filtered, and then evaporated to dryness in vacuo to give benzyl (1S,2R)-2-(hydroxymethyl)-4-oxocyclohexylcarbamate (1.80 g) as a clear viscous oil after drying under vacuum overnight: 1H NMR (300 MHz, CDCl3) δ 7.37 (s, 5H), 5.57 (d, J=6.9 Hz, 1H), 5.13 (s, 2H), 4.25 (br s, 1H), 3.69 (m, H), 3.45 (m, 2H), 2.38-2.02 (m, 7H).

Provenance & Evidence