HCID 178523817, compound → Benzyl (4-oxocyclohexyl)carbamate

Participants

Reaction Steps

To a stirred solution of trans-4-benzyloxycarbonylaminocyclohexanol (21.5 g, 86.3 mmol) in acetic acid (160 mL) at room temperature under nitrogen was added chromium trioxide (8.63 g, 86.3 mmol). After 1 d, the reaction mixture was evaporated under vacuum to yield a residue. The residue was suspended in acetone and filtered through a plug of Celite®. The filtrate was evaporated to obtain a green solid. The green solid was purified by silica gel chromatography (eluted with 5% methanol in methylene chloride) to obtain the title compound (16.65 g, 78%) as an off-white solid. 13C NMR (400 MHz, CDCl3) δ 209.6, 155.8, 136.2, 128.5, 128.2, 128.1, 66.8, 47.9, 38.8, 32.1. 1H NMR (400 MHz, CDCl3) δ 7.34 (m, 5H), 5.09 (s, 2H), 4.84 (br s, 1H), 3.97 (s, 1H), 2.38 (m, 4H), 2.20 (m, 2H), 1.68 (m, 2H). HPLC/MS [M+H]+, 248.

Provenance & Evidence