Water → tert-butyl N-(4-hydroxycyclopent-2-en-1-yl)carbamate

Participants

Reaction Steps

Molybdenum hexacarbonyl (1.46 g, 5.53 mmol) was added to a solution of the bicycle 2 (0.70 g, 3.55 mmol) in a 7:1 mature of acetonitrile and water (24 cm3). The suspension was stirred for 10 minutes at room temperature, then sodium borohydride (0.07 g, 1.85 mmol) was added and the suspension was heated under reflux for 3 hours. Upon completion of reaction, the mixture was allowed to cool to room temperature, filtered through a celite plug, and evaporated to dryness to give a dark oil. Flash chromatography (SiO2, 50% ethyl acetate in petrol) gave the alcohol 3 (0.46 g, 2.31 mmol, 65%) as a colourless oil; δH (200 MHz, CDCl3) 5.97 (1H, m, CH═CH), 5.85 (1H, dt, J 5.8 & 1.8 Hz, CH═CH), 4.80 (1H, m), 4.69 (1H, m), 4.42 (1H, m), 2.74 (2H, dt, J 14.3 & 7.1 Hz, CH2), 1.55 (1H, m, OH), 1.44 (9H, s, CO2C(CH3)3); m/z (CI) Found [MH]+ 200.1285 ([MH]+ C10H18NO3 requires 200.1287).

Provenance & Evidence