Acetone → Tert-butyl 8-tert-butyl-10-(1,2-dihydroxyethyl)-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate

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Reaction Steps

To tert-butyl 4-tert-butyl-2-vinyl-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate (1.00 g, 2.95 mmol) and 4-methylmorpholine 4-oxide (381 mg, 3.25 mmol) in acetone (9.0 mL) and water (1.0 mL) was added a solution of osmium tetroxide in 2-methyl-2-propanol (370 μL of 2.5% w/w, 0.0295 mmol) and the solution stirred 2 h. The reaction quenched with 300 mL of 1 M sodium bisulfate and stirred for 5 min. The mixture was extracted with ethyl acetate (2×200 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to provide tert-butyl 8-tert-butyl-10-(1,2-dihydroxyethyl)-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate as a white foamy solid. The crude material was taken directly to the next step. ESI-MS m/z calc. 372.3. Found 373.3 (M+1)+; Retention time: 0.83 minutes (3 min run).

Provenance & Evidence