Phenylmethyl[(3s)-3-pyrrolidinylmethyl]carbamate → phenylmethyl[((3S)-1-{(2S)-2-hydroxy-2-[6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]carbamate

Participants

Reaction Steps

To a solution of phenylmethyl[(3S)-3-pyrrolidinylmethyl]carbamate (0.53 g, 2.27 mmole) and LiClO4 (0.24 g, 2.27 mmole) in DMF (1 mL) was added 2-(methyloxy)-8-[(2S)-2-oxiranyl]-1,5-naphthyridine (0.45 g, 2.25 mmole). After 24 h at 80° C., the reaction contents were purified on silica gel (CHCl3/MeOH, 9:1, containing 5% NH4OH) to afford the title compound (0.24 g, 25%) as a light yellow oil: LC-MS (ES) m/e 437 (M+H)+.

Provenance & Evidence