Hydroquinone → 3-Bromo-2-methyl-3b,4,6,7,7a,8-hexahydro-1-thia-5-aza-cyclopenta[alpha]indene-5-carboxylic acid ethyl ester

Participants

Reaction Steps

A solution of the product from step c) (411 mg, 1.55 mmol) in AcOH (3.8 ml) and CHCl3 (3.8 ml) was treated with hydroquinone (5 mg) and NBS (331 mg, 1.86 mmol) at 40° C. for 3 hours in the dark. Next, the reaction mixture was carefully quenched with sat. NaHCO3 (5 ml) and extracted with EtOAc (3×20 ml). The combined organic extracts were dried (MgSO4) and solvent evaporated in vacuo leaving the crude product that was purified by preparative TLC (hexanes:EtOAc-1:1) to give the subtitle compound. MS calculated for C14H18BrNO2S+H 344, observed 344, 346.

Provenance & Evidence