Ethyl Acetate → 5,6-Dihydroxybicyclo[2.2.1]hept-2-yl acetate

Participants

Reaction Steps

To a solution of acetic acid bicyclo[2.2.1]hept-5-en-2-yl ester (10 mmol) and N-methyl morpholine N-oxide (22 mmol) in acetone (50 mL) and water (5 mL) was added osmium tetroxide (1.2 mL 2.5% by weight solution in t-butanol). The reaction mixture is allowed to stir at room temperature for 18 h and the acetone was stripped. Ethyl acetate (50 mL) and saturated sodium bicarbonate solution (50 ml) were added. The aqueous layer was extracted with ethyl acetate (4×50 mL). The combined organic extracts were washed with 1N aqueous HCl solution (2×50 mL) and the organic layer was dried over MgSO4, filtered and concentrated to afford a yellow oil (8.3 mmol). 1H NMR (CDCl3, 400 MHz) δ 4.82 (m, 1H), 4.18 (m, 1H), 3.80–3.55 (br s, 3H), 2.40 (m, 2H), 2.00 (s, 3H), 1.80 (s, 1H), 1.19 (s, 2H), 0.80 (m, 1H); APCl MS m/z 187.3 (M+H)+.

Provenance & Evidence