Water → tert-butyl (1R,2R)-1-(6-bromopyridin-2-yl)-2-hydroxy-2-(3-methoxyphenyl)ethylcarbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl carbamate (109 mg, 0.931 mmol) in acetonitrile (5 mL) at 0° C. was added tert-butyl hypochlorite (0.105 mL, 0.93 mmol). After stirring for 5 min, the reaction was treated with silver oxide (108 mg, 0.465 mmol). After stirring for 10 min, the resulting suspension was treated with (E)-2-bromo-6-(3-methoxystyryl)pyridine (180 mg, 0.620 mmol), osmium tetroxide (0.1 mL, 0.32 mmol), and water (0.025 mL, 1.37 mmol). The ice bath was removed and stirring continued for 8 h. The reaction was filtered and treated with a solution of sodium sulfite (5% in water, 1.5 mL). The resulting solution was heated to 50° C. and held there for 8 h. The reaction was cooled to room temperature and diluted with ethyl acetate. The organics were washed with water, then brine, dried over magnesium sulfate, concentrated, and purified by column chromatography (25% EtOAc/Hex). HNMR of the purified material suggested that it was ca. 1:1 mixture of regioisomers. The product (114 mg, 43%) was used as a mixture of regioisomers. Mass spec.: 423.09 (MH)+.

Provenance & Evidence