benzyl N-(azetidin-3-ylmethyl)carbamate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of phenylmethyl (3-azetidinylmethyl)carbamate (0.61 g, 2.76 mmole) in EtOH (1 mL) was added 8-ethenyl-7-fluoro-2-(methyloxy)-1,5-naphthyridine (673 mg, 3.3 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 (440 mg, 37%) as a light yellow oil: LC-MS (ES) m/e 425 (M+H)+. the reaction contents were purified on silica gel (CHCl3/MeOH, 9:1, containing 5% NH4OH)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1,1-dimethylethyl 3-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-azetidinecarboxylate (17.2 mmoles, 5.5 g) in DCM (100 mL) at RT was added TFA (50 mL). After 2 h, the reaction solution was concentrated under vacuum and purified on silica (CHCl3/MeOH, 9:1 containing 5% NH4OH) to give the title compound (3.59 g, 95%) as a light yellow oil: LC-MS (ES) m/e 221 (M+H)+. the reaction solution was concentrated under vacuum purified on silica (CHCl3/MeOH, 9:1 containing 5% NH4OH)