Hydrochloric Acid → ((2R,4S)-1-[(4-Methylphenyl)sulfonyl]-4-{[(4-methylphenyl)sulfonyl]oxy}pyrrolidinyl)methyl 4-methylbenzenesulfonate

Participants

Reaction Conditions

Reaction Steps

To an ice-cold solution of 219.2 g (0.808 mole) of 2R, 4S-1-(4-toluenesulfonyl)-2-hydroxymethyl-4-hydroxy-pyrrolidine (6) in 1 L of pyridine were added 539.2 g (2.828 mole) of 4-toluenesulfonyl chloride in one portion. The temperature rose to 50° C. The mixture was cooled at 10° C. and kept for 2 hours at this temperature and then at room temperature overnight. The mixture was pured into 5 L of 2.4N hydrochloric acid. After cooling, a precipitate was collected, washed with cold water, dried under reduced pressure. This presicpitate was taken up with 1 L of ethanol, filtered and washed with cold ethanol, dried under reduce pressure to give 406 g (86%) of the titled compound. M.P. =134° C. [α]D =+57.13° (c=1.9, acetone).

Provenance & Evidence