Methanol → HCID 86707210, compound

Participants

Reaction Steps

Dissolve methyl 4-[(1S)-1-[[(2R)-1-(1-methyl-2-phenoxyethyl)piperidinium-2-carbonyl]amino]ethyl]benzoate trifluoroacetate (24 mg, 0.045 mmol) in THF (226 μL) and treat the mixture with methanol (226 μL) and sodium hydroxide (1 N aqueous solution, 170 μL, 0.17 mmol). Stir the mixture overnight at room temperature, then concentrate under reduced pressure to furnish a gummy solid. Subject the crude material to reverse-phase chromatography on C18 silica gel, eluting with 0.1% TFA in a gradient of 5% to 50% ACN/water to furnish two separate fractions, each containing a separate diastereomer of product. Concentrate each fraction under reduced pressure, dissolve each in a minimal volume of methanol, triturate each with diethyl ether (5 mL), and concentrate each under reduced pressure to furnish Isomer 1 (3.0 mg, 13% yield) and Isomer 2 (1.1 mg, 5% yield) of the title compound as white solids.

Provenance & Evidence