8-Ethenyl-7-fluoro-2-(methoxy)-1,5-naphthyridine → (+/-)-Phenylmethyl[(cis-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]carbamate

Participants

Reaction Steps

To a stirred solution of 8-ethenyl-7-fluoro-2-(methyloxy)-1,5-naphthyridine (0.73 g, 3.60 mmole) in EtOH (5 mL) was added (±)-phenylmethyl{[cis-4-hydroxy-3-pyrrolidinyl]methyl}carbamate (0.90 g, 3.60 mmole). After 24 h at 80° C. the reaction contents were purified on silica (CHCl3/MeOH, 9:1 containing 5% NH4OH) affording the title compound (1.57 g, 96%) as a light yellow foam: LC-MS (ES) m/e 455 (M+H)+.

Provenance & Evidence