Réaction #66320

Équation de réaction

(2S,4R)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

3-nitrobenzenesulfonyl chloride

→

solid

Rendement 103.1%

(2S,4R)-4-(3-Nitro-benzenesulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Rendement 103.1%

Solvants

DCM

Conditions de réaction

Traitement

1. 1
   ExtractionThe reaction mixture was then extracted with 0.1 N aqueous HCl (50 mL) and aqueous Na2CO3 (50 mL) and brine (50 mL)
2. 2
   SéchageThe organic layer was dried over Na2SO4
3. 3
   Filtrationfiltrated
4. 4
   Autreevaporated to dryness

Mode opératoire

(2S,4R)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (5.0 g) was dissolved in DCM (50 mL) and 3-nitrobenzenesulfonyl chloride (4.8 g) was added. This solution was cooled to 5° C. and the TEA (8.52 mL) was carefully added. The reaction mixture was stirred at 25° C. for 18 h. The reaction mixture was then extracted with 0.1 N aqueous HCl (50 mL) and aqueous Na2CO3 (50 mL) and brine (50 mL). The organic layer was dried over Na2SO4, filtrated and evaporated to dryness to yield a light brown amorphous solid (9.05 g). MS: m/z=431.4 [M+H]+.

Source