Cyclobutanone → Tert-butyl [2-(1-hydroxycyclobutyl)phenyl]carbamate

Participants

Reaction Steps

To phenyl-carbamic acid tert-butyl ester (2 g, 10.4 mmol) in ether (30 mL) at 0° C. was added t-BuLi (15 mL, 26 mmol, 1.7 M) and the reaction solution stirred for 3 hours prior to the addition of cyclobutanone (1.2 mL, 15.6 mmol). The reaction mixture was allowed to warm to room temperature. Upon completion by thin-layer chromatography (TLC), the reaction was poured into ice-cold saturated ammonium chloride (100 mL) and extracted with ethyl acetate (50 mL). The organics were dried over sodium sulfate, concentrated, and purified on a silica gel column (10% ethyl acetate/hexane) to give tert-butyl [2-(1-hydroxycyclobutyl)-phenyl]carbamate (0.86 g, 32%) as a white solid. 1H NMR (DMSO-d6): δ 8.48 (s, 1H), 7.8 (d, 1H, J=7.92 Hz ), 7.35 (dd, 1H, J=7.7, 1.4 Hz), 7.25 (td, 1H, J=7.5, 1.6 Hz), 7.03 (td, 1H, J=7.5, 1.3 Hz), 2.51-2.49 (m, 2H), 2.43-2.39 (m, 2H), 2.28-2.25 (m, 2H), 1.45 (s, 9H). MS (ESI) m/z 190 ([M+H]+); MS (ESI) m/z 188 ([M−H]−);

Provenance & Evidence