Propargyl bromide → 4-Propargyl-4-azatricyclo[4.3.1.13,8]undecan-5-one

Participants

Reaction Conditions

Reaction Steps

A solution of potassium hydroxide (0.56 gram, 10 mmol) in 3 ml of absolute methanol was added to 4-azatricyclo[4.3.1.13,8 ]undecan-5one (1.65 gram, 10 mmol) and the solvent was slowly removed under reduced pressure with the internal temperature not exceeding 25° C. When solid began to separate, anhydrous toluene was added and the solvent removal continued (a total of 30 ml of toluene were removed), then the temperature was raised to 90° C. (with the distillation continuing at atmospheric pressure--a total of 10 ml of toluene were distilled). The reaction mixture was cooled to 40° C. and propargyl bromide (0.9 ml, 10 mmol) was added dropwise. The temperature was raised to 65° C. and the mixture stirred for 4 hours. The solid precipitate was filtered off, and the filtrate was evaporated to yield 1.82 gram of compound 5a. Melting point 168°-170° C. (recrystallized from a petr. ether-ethanol 10:1 mixture by volume).

Provenance & Evidence