Carbon Dioxide → HCID 70802833, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 1-(S)-(2-(6-bromobenzo[d]isoxazol-3-yl)phenyl)-2-(pyridin-2-yl)ethylcarbamate (Compound 16a) (1.72 g) in diethyl ether (30 mL) at 5° C. was added a 60% dispersion in mineral oil of sodium hydride (3.34 g). The suspension was stirred at 5° C. for 10 min and then cooled to −65° C. and a 2.5M solution of n-butyllithium in hexanes (5.57 mL) was added. The suspension was stirred at −70° C. for 30 min and then poured onto solid carbon dioxide pellets and left to stand until the mixture reached room temperature. To this was added water and acidified with citric acid and extracted with ether (3×200 mL), the organic layers were dried over anhydrous magnesium sulfate and evaporated. Flash chromatography eluting with 10% methanol in dichloromethane to give the title product (0.71 g).

Provenance & Evidence