Quinoline → (2S,4R)-Pyrrolidin-1-yl-[2-(2,4,5-trifluoro-benzyloxymethyl)-4-tritylsulfanyl-pyrrolidin-1-yl]-methanone

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Reaction Steps

A solution of 0.02 ml (0.18 mmol) trichloromethylchloroformate in 3 ml CH2Cl2 was treated at 0° C. with 0.04 ml (0.37 mmol) quinoline and after 15 min with 0.17 g (0.33 mmol) (2S,4R)-2-(2,4,5-trifluoro-benzyloxymethyl)-4-tritylsulfanyl-pyrrolidine in 2 ml CH2Cl2. After 2 h, the reaction was evaporated and redissolved in 15 ml CH2Cl2 and treated at 0° C. with 0.14 ml (1.65 mmol) pyrrolidine and stirred for 30 min. The reaction was extracted with aqueous 10% KHSO4/Et2O (3×) and the organic phase was dried over Na2SO4. Evaporation and precipitation from Et2O/pentane gave 121 mg (59%) (2S,4R)-Pyrrolidin-1-yl-[2-(2,4,5-trifluoro-benzyloxymethyl)-4-tritylsulfanyl-pyrrolidin-1-yl]-methanone, MS: 617 (M+H+).

Provenance & Evidence