Aluminum(III) Chloride → 5-Benzyl-3b,4,5,6,7,7a-hexahydro-3-thia-5-aza-cyclopenta[alpha]inden-8-one

Participants

Reaction Steps

A solution of the product from step d) (2.9 g, 8.15 mmol) in CH2Cl2 (12 ml) was added dropwise to a slurry of AlCl3 (3.26 g, 24.5 mmol) in CH2Cl2 (28 ml) at 22° C. After 45 minutes, the reaction mixture was poured into ice cold 2 M NaOH (100 ml) and extracted with CH2Cl2 (300 ml). The organic extract was dried (MgSO4), solvent evaporated in vacuo, and residue purified by silica-gel chromatography using a ethyl acetate/hexanes gradient (0% to 50% ethyl acetate) to give the subtitle compound (1.32 g, 57%). MS calculated for C17H17NOS+H 284, observed 284.

Provenance & Evidence