Ozone → HCID 68688454, compound

Participants

Reaction Steps

To a stirring solution of N-(t-butoxycarbonyl)-(R)-1,3,4,10b-tetrahydro-9-(cis-1-propenyl)-7-trifluoromethyl-pyrazino[2,1-a]isoindol-6(2H)-one (182 mg, 0.46 mmol) in MeOH (5.0 mL) at −78° C. was bubbled ozone for 5 min. until the reaction turned a light blue color. After 5 min., sodium borohydride (23 mg, 0.6 mmol) was added. The reaction was stir for 1 hr and then warmed to room temp. The reaction was conc. in vacuo to a white solid and then dissolved in 1M aq. HCl. After 15 min, the reaction was diluted with EtOAc, basefied with NaHCO3, and treated with di-t-butyl dicarbonate (125 mg, 0.58 mmol). After 1 h, the reaction was extracted with EtOAc (3×5 mL). The organic layers were combined, dried over Na2SO4, and conc. in vacuo to a colorless oil. The oil was purified by flash chromatography (silica gel, 0–50% EtOAc in hexanes) to give 141 mg of the desired product as a white solid. MS (ESI) 387 (M+H).

Provenance & Evidence