Thionyl Chloride → 1,2,3,3a,8,8a-Hexahydroindeno[1,2-c]pyrrole

Participants

Reaction Steps

3,3a,8,8a-Tetrahydro-2H-2-aza-cyclopenta[a]inden-1-one. Thionyl chloride (1.9 mL, 26.4 mmol) was added to a solution of 2,2a,7,7a-tetrahydro-cyclobuta[a]inden-1-one oxime (1.5 g, 8.8 mmol) in 1,4-dioxane (44 mL), and stirred overnight at room temperature. The reaction was quenched with saturated aqueous NaHCO3 (100 mL), and extracted with EtOAc (3×50 mL). The organic extracts were washed with brine, dried over MgSO4, and concentrated to give the subtitle compound and its regioisomer, which were used without further purification. MS calculated for C11H11NO+H: 174, observed: 174.

Provenance & Evidence