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

Participants

Reaction Conditions

Reaction Steps

To tert-butyl carbamate (688 mg, 5.88 mmol) in propanol (10 mL) was added sodium hydroxide (231 mg, 5.78 mmol) in water (20 mL) followed by tert-butyl hypochlorite (0.652 mL, 5.78 mmol). The solution was cooled to 0° C. and (DHQD)2PHAL (89 mg, 0.114 mmol) was added in propanol (3 mL) followed by (E)-2-bromo-6-(3-methoxystyryl)pyridine (550 mg, 1.90 mmol) in propanol (10 mL). To this was added potassium osmate dihydrate (27.9 mg, 0.076 mmol) as a solid in one portion. The reaction was allowed to gradually warm to room temperature overnight. The reaction was placed in a cool bath (ca. 15° C.) and quenched by addition of sodiumthiosulfate (1.1 g) in water (8 mL). The reaction was stirred at room temperature for 30 min. The reaction was diluted with 1:1 diethylether/ethyl acetate, washed with water (2×), then brine, dried over magnesium sulfate, and concentrated. Column chromatography (20%-->50% EtOAc/Hex) gave 860 mg (107% yield) as a mixture of regioisomers. Mass spec.: 444.98 (MNa)+.

Provenance & Evidence