Acetone → (3,4-Dihydroxycyclopentyl)methyl 4-nitrobenzoate

Participants

Reaction Steps

Osmium tetroxide (235 μL, 0.75 mmol) was added to a solution of cyclopent-3-en-1-ylmethyl 4-nitrobenzoate (3.70 g, 15.0 mmol) and 4-methylmorpholine N-oxide (1.93 g, 16.5 mmol) in tent-butanol (6.7 mL)/water (40 mL)/acetone (13.3 mL). The solution was stirred at room temperature for 16 hours. Aqueous sodium bisulfite solution was added, and the solution was stirred for 30 min. The solution was then extracted with ethyl acetate, and the combined organic layers were dried (magnesium sulfate), filtered, and concentrated in vacua. The residue was purified by silica gel chromatography (Biotage 65i), eluting with 0-100% ethyl acetate/hexanes to give the title compound as a colorless oil. 1H NMR (500 MHz, CHCl3) δ 1.67-1.75 (m, 2H), 1.95-2.00 (m, 2H), 2.80-2.85 (m, 1H), 4.21 (quintet, J=4.1 Hz, 2H), 4.26 (d, J=6.7 Hz, 2H), 8.19 (d, J=8.7 Hz, 2H), 8.29 (d, J=8.7 Hz, 2H).

Provenance & Evidence