Sodium Hydroxide → HCID 86673407, compound

Participants

Reaction Conditions

Reaction Steps

To tert-butyl carbamate (2.094 g, 17.88 mmol) in propanol (24 mL) was added sodium hydroxide (0.703 g, 17.59 mmol) in water (45 mL) followed by tert-butyl hypochlorite (1.99 mL, 17.59 mmol). The solution was cooled to 0° C. and treated with a solution of (DHQD)2PHAL (0.112 g, 0.144 mmol) and (DHQ)2PHAL (0.112 g, 0.144 mmol) in propanol (21 mL). The reaction was diluted with propanol (30 ml), and treated with (E)-2-bromo-6-styrylpyridine (1.5 g, 5.77 mmol) as a solid in one portion. To this was added potassium osmate dihydrate (0.085 g, 0.231 mmol) as a solid in one portion. The ice bath was removed and stirring continued for 1.5 h at room temperature. The reaction was placed in a cool bath (ca. 15° C.) and quenched by addition of sodiumthiosulfate (2.1 g) in water (12 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 1.1 g (49%) as a mixture of regioisomers. The reaction was azeotroped with toluene and pumped under high vacuum (2 cycles) to aid in the removal of an unknown impurity. The material was used without additional purification. Mass spec.: 393.1 (MH)+.

Provenance & Evidence