Chloroform → 2-Bromo-3b,4,5,7,7a,8-hexahydro-3-thia-6-aza-cyclopenta[alpha]indene-6-carboxylic acid ethyl ester

Participants

Reaction Steps

A solution of the product from step h) (722 mg, 2.88 mmol) in AcOH (7.2 ml) and CHCl3 (7.2 ml) was treated with NBS (529 mg, 2.97 mmol) at 22° C. for 30 minutes. Next, the reaction was carefully quenched with sat. NaHCO3 (10 ml), extracted with EtOAc (2×75 ml) and the combined organic extracts were dried (MgSO4) and solvent evaporated in vacuo leaving the crude product that was purified by silica-gel chromatography using a ethyl acetate/hexanes gradient (10% to 50% ethyl acetate) to give the subtitle compound. MS calculated for C15H20BrNO2S+H 358, observed M-tBu 302, 304.

Provenance & Evidence