Sodium Hydroxide → HCID 86673420, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl carbamate (189 mg, 1.612 mmol) in propanol (7 mL) was added sodium hydroxide (54.1 mg, 1.352 mmol) in water (4 mL) followed by tert-butyl hypochlorite (172 mg, 1.586 mmol) (freshly prepared following an org synthesis prep). After 5 min the solution was cooled to 0° C. and treated with a solution of (DHQD)2PHAL (20.26 mg, 0.026 mmol) in propanol (4 mL). To this solution was added a solution of (E)-5-bromo-2-fluoro-3-(4-(trifluoromethyl)styryl)pyridine (180 mg, 0.520 mmol) in propanol (10 mL). To this solution was added potassium osmate dihydrate (7.66 mg, 0.021 mmol) in one portion. The reaction turned light orange and was allowed to stir at 0° C. overnight allowing the reaction to warm up to room temperature. 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 25% EtOAc/75% Hexanes to 50%/50% EtOAc/Hexanes to afford tert-butyl (1R,2R)-1-(5-bromo-2-fluoropyridin-3-yl)-2-hydroxy-2-(4-(trifluoromethyl)phenyl)ethylcarbamate (250 mg, 0.530 mmol, 99% yield) as an inseparable mixture with its regioisomer. LC/Mass spec. (Analytical HPLC method 2): RT=2.78 min. Mass=503.07 (MNa)+.

Provenance & Evidence