Ethylamine → HCID 19737966, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the product of Step D (1.4 g , 3 mmol) and triethylamine (1.7 mL, 12 mmol) in THF (10 mL) at -20° C. was added p-toluenesulfonyl chloride (1.2 g, 6 mmol) and the reaction mixture was stirred at 0° C. for 5 hr. The reaction mixture was cooled to -78° C. at which point ethylamine (10 mL) was added; this mixture was allowed to warm to reflux temperature for 2 hr and then maintained at room temperature for 40 hr. After removing the solvent the crude product was diluted with ethyl acetate (150 mL), washed with water (2×50 mL) and brine (2×50 mL), dried (MgSO4), and evaporated to a syrup which was purified by column chromatography [silica; CH3OH/CH2Cl2 (20:1)] to give 900 mg (64%) as a colorless foam.

Provenance & Evidence