Potassium Iodide → 6-Cyclopropoxy-2,3-dihydro-1H-3a-aza-cyclopenta[a]indene

Participants

Reaction Conditions

Reaction Steps

6.00 g sodium hydride 55-65% in oil in portion was added during ca 30 min at room temperature to a solution of 23.5 g 2,3-dihydro-1H-3a-aza-cyclopenta[a]inden-6-ol in 200 mL dimethylsulfoxide. 18.75 g potassium carbonate and 1.700 g potassium iodide and 34 mL cyclopropylbromide was added to the resulting solution. The resulting suspension was stirred under argon at 100° C. for 48 h. Another 17 mL cyclopropylbromide was added. The resulting suspension was stirred under argon at 100° C. for 24 h. The reaction mixture was diluted with water and extracted with dichloromethane. The organic phase was purified by chromatography on silica gel with hexane:dichloromethane=1:1 to yield 17.75 g 6-Cyclopropoxy-2,3-dihydro-1H-3a-aza-cyclopenta[a]indene as a white crystalline solid melting at 61-63° C.

Provenance & Evidence