Ammonia → HCID 54597137, compound

Participants

Reaction Steps

2-[4-((2S,3′S)-2-Methyl-[1,3′]bipyrrolidinyl-1′-yl)-phenyl]-N-piperidin-4-yl-acetamide hydrochloride (0.51 g, 1.38 mmol) was dissolved in THF (20 mL) and water (5 mL) to form a clear solution. To this solution was added 0.30 g of ethyl chloroformate (3 mmol, 2 equiv), followed by K2CO3 (0.76 g, 5.52 mmol, 4 equiv). The clear solution was stirred at rt overnight. TLC (5% of 7N NH3 in MeOH/DCM) showed the SM was consumed completely. LCMS: a single peak at 2.559 with MS of 443 was detected. The two layers were separated and the aqueous layer was extracted with EtOAc (2×10 mL). The combined organic solution was washed with brine (2×10 mL), dried (K2CO3), filtered, and concentrated. The crude product was purified on a 25-g silica gel column to get 0.42 g (69%) of the title compound as a tan solid.

Provenance & Evidence