Water → 3-Pyrrolidinol, 1-[(4-methylphenyl)sulfonyl]-, 3-(4-methylbenzenesulfonate), (3S)-

Participants

Reaction Conditions

Reaction Steps

(S)-3-pyrrolidinol (30 g, 0.344 moles) was dissolved in toluene (150 ml) and tetrabutylammonium bromide (3.39 g, 0.0105 moles) was added to the solution. p-Toluensulfonylchloride (140.94 g, 0.7393 moles) was then added portion-wise to the solution, causing the temperature of the solution to rise to 35 to 40° C. Then, 30% NaOH (112.1 g, 0.8407 moles) was slowly added to the solution over about 1 hour, causing the temperature of the solution to rise to 55 to 60° C. After maintaining the solution for 5 hours at 55-60° C., the reaction was complete. Water (30 ml) was then added, and the resulting suspension was cooled to 0° C. over 1 hour to give a solid. The solid was filtered and washed with cold toluene and water to give the title compound. (Dry weight 127.95 g, yield 94%, HPLC purity 99.2% area). The main impurity is 1-tosyl-3-(S)-pyrrolidinol (reaction intermediate) in an amount of 0.05% area by HPLC.

Provenance & Evidence