Sodium Carbonate → (RS)-3-(4-hydroxy-phenylsulfanyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

(RS)-3-(Toluene-4-sulfonyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.8 g, 2.34 mmol), 4-mercaptophenol (0.49 g, 3.88 mmol, 90%) and Na2CO3 (0.37 g, 3.51 mmol) were suspended in acetonitrile (10 ml). After 20 hours refluxing, reaction mixture was concentrated. The residue was taken up in H2O (15 ml) and extracted with CH2Cl2 (3 times). The combined organic phases were dried over Na2SO4, filtered and the solvent was evaporated. The residue was chromatographed over silica gel (hexane-ethylacetate 4:1 then 2:1) to provide (RS)-3-(4-hydroxy-phenylsulfanyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.56 g, 81%) as a slightly yellow solid, MS: m/e=296.4 (M+H+).(RS)-3-(Toluene-4-sulfonyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester is a known compound and has been prepared as described in WO 9734895.

Provenance & Evidence