Sodium Hydroxide → HCID 86762311, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl carbamate (1.907 g, 16.28 mmol) in propanol (4.6 mL) was added sodium hydroxide (0.641 g, 16.02 mmol) in water (8 mL) followed by tert-butyl hypochlorite (1.808 ml, 16.02 mmol). After 5 minutes, the solution was cooled to 0° C. and treated with a solution of (DHQD)2PHAL (0.245 g, 0.315 mmol) in propanol (4.6 mL). To this was added a solution of (Z)-3-bromo-5-(2-phenylprop-1-enyl)pyridine and (E)-3-bromo-5-(2-phenylprop-1-enyl)pyridine (1.440 g, 5.25 mmol) in propanol (7.8 mL), and potassium osmate dihydrate (0.077 g, 0.210 mmol) as a solid in one portion. The ice bath was removed and stirring continued overnight. The reaction was quenched by addition of a solution of sodium thiosulfate (1.84 g) in water (23 mL). After 30 minutes, the reaction was diluted with ether, washed with water, then brine, dried over MgSO4, and concentrated. Biotage purification (20%-50% EtOAc/Hex) gave title compound (1.18 g, 2.90 mmol, 55% yield) as colored semi-solid. Mass spec.: 407.0 (MH)+.

Provenance & Evidence