Potassium Carbonate → 2-(3-Chloro-4-cyclopentylsulfanyl-phenyl)-n-((1r,2r)-2-hydroxy-1-methyl-2-phenyl-ethyl)-n-methyl-acetamide

Participants

Reaction Conditions

Reaction Steps

To a three neck round bottom flask is added a stir bar, dropping funnel, argon inlet and thermometer. It is then charged (3-chloro-4-cyclopentylsulfanyl-phenyl)-acetic acid (5.00 mmol), acetone (15 mL) and potassium carbonate (3.0 equiv.) and cooled to −10° C. To this cooled solution is then added trimethylacetyl chloride (1.05 equiv.) dropwise slowly to keep the temperature below −10° C. throughout the addition. It is then stirred at −10° C. for 15 min, then warmed to 0° C. and stirred for an additional 10 min and then recooled to −10° C. To the reaction is then added (1R,2R)-(−)-pseudoephedrine (1.5 equiv.) in one portion. It is then stirred at −10° C. for 10 min and then warmed to 25° C. and stirred for 1 h. After such time, the reaction is quenched with water (10 mL) and poured into a separatory funnel and added ethyl acetate (25 mL). The layers are separated and the organic layer is washed with water (2×10 mL) and the organic layers are then back extracted with ethyl acetate (3×25 mL) dried over magnesium sulfate, filtered and concentrated in vacuo. Purification on an AnaLogix Intelliflash system (silica gel cartridge) will afford 2-(3-chloro-4-cyclopentylsulfanyl-phenyl)-N-((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-N-methyl-acetamide.

Provenance & Evidence