Water → 1-(4-Toluenesulfonyl)-4-(4-toluenesulfonyloxy)-D-proline ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a cold solution of 11.85 g (38 mmoles) 1-(4-toluenesulfonyl)-4-hydroxy-D-proline ethyl ester in 37 mL pyridine at 0° C. was added 8.0 g (41 mmoles) of 4-toluenesulfonyl chloride portionwise in 15 minutes. The cold solution was stirred one hour at 0° C. and then 48 h at room temperature. Water (100 mL) was added dropwise in the solution cooled at 0° C. which was stirred 30 minutes at 0° C. The precipitate was filtered and washed with cold water and ether to give 15.55 g of titled compound. MP 122° C. [α]20 =+26.36° (c=2, chloroform)

Provenance & Evidence