Sodium Hydroxide → HCID 70958312, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl carbamate (1431 mg, 12.22 mmol) in propanol (10 mL) was added sodium hydroxide (481 mg, 12.02 mmol) in water (4 mL) followed by tert-butyl hypochlorite (1305 mg, 12.02 mmol). After 5 min the solution was cooled to 0° C. and treated with a solution of (DHQD)2PHAL (154 mg, 0.197 mmol) in propanol (4 mL). To this solution was added a solution of (E)-5-bromo-2-fluoro-3-(4-fluorostyryl)pyridine (1167 mg, 3.94 mmol) in propanol (10 mL). To this solution was added potassium osmate dihydrate (58.1 mg, 0.158 mmol) in one portion. The reaction turned light orange and was allowed to stir at 0° C. for 1 hr. The ice bath was then removed and the reaction was allowed to warm to room temperature and stirred over night. The reaction was quenched with a 10% solution of sodium thiosulfate and stirred for 30 min. The reaction was then extracted with diethylether (3×). The combined organic extracts were combined washed with water, then brine. The organic layer was separated, dried over sodium sulfate and evaporated in vacuo. The crude residue was purified by silica gel chromatography 5% acetone/95% Hexanes to 50%/50% Acetone/Hexanes to afford tert-butyl (1R,2R)-1-(5-bromo-2-fluoropyridin-3-yl)-2-(4-fluorophenyl)-2-hydroxyethylcarbamate (1450 mg, 3.38 mmol, 86% yield) along with its regioisomer as an inseparable mixture. LC/Mass spec. (Analytical HPLC method 2): RT=2.07 min. Mass=429.30 (MH)+.

Provenance & Evidence