Ammonium formate → 6-Hydroxy-3-[3-methoxy-4-(1-pyrrolidinylmethyl)benzyl]-2-[4-[4-methoxy-4-oxobutoxy]phenyl]benzo[b]thiophene

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6-Benzyloxy-3-[3-methoxy-4-(1-pyrrolidinylmethyl)benzyl]-2-[4-(4-methoxy-4-oxobutoxy)phenyl]benzo[b]thiophene (147 mg) in THF (3.0 mL) was treated sequentially with a solution of ammonium formate (25% in H2O, 2.0 mL) and 10% palladium on carbon (100 mg) at ambient temperature. The resulting mixture was stirred at ambient temperature under argon for 3 h before it was filtered through diatonaceous earth followed by rinsing with dichloromethane and methanol. The filtrate was extracted with dichloromethane (20 mL×3) from water (30 mL). The combined organic layers were dried with sodium sulfate and concentrated under reduced pressure. Chromatography with Et3N:EtOAc (0-5%) afforded the product (108 mg).

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