HCID 178418287, compound → tert-butyl N-(4-oxocyclohexyl)carbamate

Participants

Reaction Steps

To a stirred solution of tert-butyl trans-4-hydroxycyclohexylcarbamate (2.0 g, 9.3 mmol) in 100 mL of dichloromethane was added PCC (3.0 g, 14 mmol) and celite (5.0 g). The reaction mixture was stirred at room temperature overnight. The reaction mixture was filtered through a celite pad and the residue concentrated under reduced pressure. The crude compound was purified by column chromatography (silica gel, 200-300 mesh, eluting with a mixture of ethyl acetate and petroleum ether (1:1, v/v) to give tert-butyl 4-oxocyclohexylcarbamate (1.6 g, 80%) as a white solid. 1H NMR (300 MHz, CDCl3): δ 4.52 (brs, 1H), 3.94 (brs, 1H), 2.45-2.40 (m, 4H), 2.20-2.27 (m, 2H), 1.74-1.63 (m, 2H), 1.46 (s, 9H).

Provenance & Evidence