Benzyl Alcohol → HCID 71117581, compound

Participants

Reaction Conditions

Reaction Steps

Phosgene (20% in toluene, 1.0 g, 2.2 mmol, 1.5 equiv) was added to a solution of cis-6-fluoro-1,2,3,3a,4,9a-hexahydro-9H-cyclopenta[b]quinolin-9-one 6B (300 mg, 1.5 mmol, 1 equiv) and diisopropyl ethylamine (380 uL, 2.2 mmol, 1.5 equiv) in THF (14.6 mL). After stirring at 23° C. for two hours the solution was treated with benzyl alcohol (450 μL, 4.4 mmol, 3 equiv) and sodium hydride (60% in mineral oil, 230 mg, 5.9 mmol, 4 equiv). After stirring at 23° C. for 12 hours the reaction was neutralized to pH=7 with 1N HCl. The reaction mixture was then partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride solution, and the washed solution was dried over sodium sulfate. The dried solution was filtered, and the filtrate was concentrated. The filtrate was purified by flash-column chromatography (hexanes, grading to 50% ethyl acetate-hexanes) to afford 6C. [M+H]+: 340.2.

Provenance & Evidence