Hydrochloric Acid → 5-Benzyl-4,5,6,7,7a,8-hexahydro-3bH-1-thia-5-aza-cyclopenta[alpha]indene

Participants

Reaction Steps

A slurry of AlCl3 (1.32 g, 9.96 mmol) in CH2Cl2 (6 ml) was treated with tert-butylaminoborane (1.73 g, 19.92 mmol) at 0° C. and stirred for 30 minutes. Next, a solution of the product from step f) (941 mg, 3.32 mmol) in CH2Cl2 (3 ml) was added dropwise to the AlCl3/borane solution. After 2 hours at 0° C., the crude reaction mixture was poured into cold 10% HCl, treated with 2 M NaOH to pH 12 and extracted with CH2Cl2 (3×75 ml). The combined organic extracts were washed with brine (75 ml), dried (MgSO4) and solvent evaporated invacuo. The crude product was purified by silica-gel chromatography using a ethyl acetate/hexanes gradient (0% to 75% ethyl acetate) to give the subtitle compound. MS calculated for C17H19NS+H 270, observed 270.

Provenance & Evidence