tert-Butanol → HCID 18428501, compound

Participants

Reaction Steps

To a stirring solution of the compound from EXAMPLE 259 (3.3 mmol) in 80 mL of acetone:H2O (3:1) is added N-methylmorpholine N-oxide (0.64 g, 4.8 mmol) and 2.5% OsO4 in t-BuOH (3.4 mL, 3.4 mmol). After 18 h, 120 mL of H2O, 8 g of celite, and 1.6 g Na2S2O4 is added to the reaction. The reaction is filtered through a pad of wet celite. To the filtrate is added 200 mL of 1M KHSO4. The filtrate is extracted with 3×200 mL EtOAc. The combined organic layers are dried, filtered, and stripped. The residue is purified by chromatography to yield the title compound.

Provenance & Evidence