Chloroacetyl chloride → HCID 86725425, compound

Participants

Reaction Steps

To a stirring solution of tert-butyl 4-(((1-(((tert-butyldimethylsilyl)oxy)methyl)cyclopropyl)amino)methyl)-4-hydroxypiperidine-1-carboxylate (1.688 mmol) and N,N-diisopropylethylamine (4.22 mmol) in anhydrous dichloromethane (30 mL) cooled to 0° C. was added neat chloroacetyl chloride (2.53 mmol). After 30 min, the reaction was diluted with saturated aq sodium bicarbonate and extracted with dichloromethane. The combined extracts were dried over magnesium sulfate and were evaporated onto silica. Purification of the solid by flash chromatography (30% ethyl acetate in hexanes) afforded the title product (742 mg, 85% yield) as a light orange oil. MS(ES)+ m/e 491.4 [M+H]+.

Provenance & Evidence