Water → HCID 86674063, compound

Participants

Reaction Steps

A solution of tert-butyl-(R)-1-(3-oxa-2-aza-bicyclo[2.2.1]hept-5-en-2-yl)-1-oxopropan-2-ylcarbamate (27.3 g, 101.75 mmol, 1.00 equiv.) in teterahydrofuran:water (5:1) (600 mL), osmium tetroxide (230 mg, 0.90 mmol, 0.01 equiv.), and N-methylmorpholine-N-oxide (25.26 g, 215.62 mmol, 2.10 equiv.) was stirred at about 20° C. for about 50 minutes. After adding sodium thiolsulfate (22 g), the resulting solution was extracted with ethyl acetate (3×200 mL) and the organic layers combined. The organic phase was washed with a saturated sodium bicarbonate solution (1×250 mL) and then concentrated in vacuo to give the desired product as a yellow liquid (30.1 g; yield=98%). 1H NMR (300 MHz, CDCl3) δ: 5.29 (b, 1H), 4.36-4.74 (m, 3H), 3.76-4.09 (m, 4H), 2.67 (m, 1H), 1.90 (m, 1H), 1.43 (s, 9H), 1.30 (d, J=6.9 Hz, 3H).

Provenance & Evidence