[CH:1]12[CH2:7][CH:4](C=C1)[CH2:3][CH:2]2[O:8]C(=O)C.C[N+]1([O-])CC[O:16]CC1.[C:20]([O:23][CH2:24][CH3:25])(=[O:22])[CH3:21].C(=O)(O)[O-].[Na+]>CC(C)=O.O.[Os](=O)(=O)(=O)=O>[OH:16][CH:1]1[CH:2]([OH:8])[CH:3]2[CH2:4][CH:7]1[CH2:25][CH:24]2[O:23][C:20](=[O:22])[CH3:21]
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)+.
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