Triacetoxyperiodinane → Benzyl 2,2-dimethyl-3-oxocyclopentylcarbamate

Participants

Reaction Steps

Dess-Martin periodinane (9.49 g, 22.39 mmol) was added to a solution of cis/trans mixture of benzyl 3-hydroxy-2,2-dimethylcyclopentylcarbamate (3.93 g, 14.92 mmol, from Step 1 of Intermediate 21) in dichloromethane (150 mL) at room temperature. After 2 h at room temperature, the mixture was filtered to remove the precipitate. The filtrate was washed with 10% aqueous sodium thiosulfate (10 mL), saturated sodium bicarbonate (20 mL), brine (20 mL), dried (MgSO4), filtered and concentrated. Silica gel chromatography, eluting with 10 to 50% ethyl acetate in hexanes, gave benzyl 2,2-dimethyl-3-oxocyclopentylcarbamate (3.20 g, 82% yield). 1H NMR (400 MHz, chloroform-d) δ ppm 7.30-7.74 (5 H, m), 4.97-5.33 (2 H, m), 4.60-4.93 (1 H, m), 2.17-2.42 (2 H, m), 1.47-1.82 (2 H, m), 1.12 (3 H, s), 0.91 (3 H, s); MS (ES+) m/z: 262.3 (M+H); HPLC retention time: 2.643 min (analytical HPLC Method A).

Provenance & Evidence