Reaction #324438

Reaction equation

(S)-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Et3N

methanesulfonyl chloride

→

3-methanesulfonyloxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Solvents

CH2Cl2

brine

Conditions

Workup

1. 1
   Extractionthe mixture extracted with CH2Cl2 (2×)
2. 2
   OtherThe combined organics were dried

Procedure

To (S)-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (2.0 g, 10.9 mmol) in CH2Cl2 (50 mL) at 0° C. was added Et3N (1.4 g, 1.9 mL, 13.4 mmol) and methanesulfonyl chloride (1.38 g, 0.94 mL, 12.1 mmol). After 1 h, brine was added and the mixture extracted with CH2Cl2 (2×). The combined organics were dried to give 3-methanesulfonyloxy-pyrrolidine-1-carboxylic acid tert-butyl ester that was used without further purification.

Source