Sodium Hydroxide → HCID 86673446, compound

Participants

Reaction Conditions

Reaction Steps

To tert-butyl carbamate (270 mg, 2.31 mmol) in propanol (3 mL) was added sodium hydroxide (91 mg, 2.27 mmol) in water (6 mL) followed by tert-butyl hypochlorite (0.256 mL, 2.27 mmol). The solution was cooled to 0° C. and (DHQD)2PHAL (34.8 mg, 0.045 mmol) was added in propanol (3 mL) followed by (E)-2-bromo-6-(2-fluorostyryl)pyridine (207 mg, 0.744 mmol) in propanol (6 mL). To this was added potassium osmate dihydrate (10.97 mg, 0.030 mmol) as a solid in one portion. The reaction was allowed to gradually warm to room temperature in the dewar overnight. The reaction was cooled to 0° C. and quenched by addition of sodiumthiosulfate (300 mg) in water (3 mL). The reaction was stirred at room temperature for 30 min. The reaction was diluted with ether, washed with water (2×), then brine, dried over magnesium sulfate, and concentrated. Column chromatography (15%→30% EtOAc/Hex) gave 375 mg (quant.). Mass spec.: 411.2 (MH)+.

Provenance & Evidence