Sodium Iodide → (2S,4R)-benzyl-[1-methanesulfonyl-4-(4-methoxy-benzylsulfanyl)-pyrrolidin-2-ylmethyl]-amine

Participants

Reaction Steps

A slurry of 300 mg (0.73 mmol) (2S,4R)-methanesulfonic acid 1-methanesulfonyl-4-(4-methoxy-benzylsulfanyl)-pyrrolidin-2-ylmethyl ester and 109 mg (0.73 mmol) of NaI in 5 ml benzylamine was heated in the oil bath to 100° C., evaporated in the kugelrohr at 50–70° C./1 Torr and extracted with aqueous saturated NaHCO3 solution/Et2O (3×). The organic phase was dried over Na2SO4, evaporated and the residue was crystallized from Et2O/pentane at −20° C. to give 200 mg (65%) of (2S,4R)-benzyl-[1-methanesulfonyl-4-(4-methoxy-benzylsulfanyl)-pyrrolidin-2-ylmethyl]-amine, mp 63–64° C., MS: 421 (MH+).

Provenance & Evidence