Trifluoroacetic acid → HCID 66865000, compound

Participants

Reaction Steps

To a solution of 4-{1-[4-(1-methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-phenoxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (1.16 g, 2.50 mmol) in dichloromethane (25 mL) is added trifluoroacetic acid (1.32 mL, 17.48 mmol). The reaction is stirred at room temperature for 18 h. The mixture is concentrated in vacuo and diluted with 3 mL of ethyl acetate. 2 M aqueous sodium hydroxide is added to produce a white solid. The solid is filtered and dried to afford 0.86 g of the title compound. MS (m/z) 365 (M+1). The title compound (0.320 g, 0.88 mmol) is separated into its enantiomers using an eluent of 0.2% dimethylethylamine in 2:3 acetonitrile:methanol on a 4.6×150 mm Chiralcel AD-H column at 1 mL/min to afford 0.115 g of isomer 1 (100% ee, RT=5.27 min) MS (m/z) 365 (M+1) and 0.112 g of isomer 2 (100% ee, RT=8.59 min). MS (m/z) 365 (M+1).

Provenance & Evidence