tert-butyl N-[(3-fluoropyrrolidin-3-yl)methyl]carbamate synthesis

Yield: 98%

Reaction Conditions:

with hydrogen;palladium dihydroxide in methanol at 20; under 760.051 Torr; for 18 h;

Steps:

66.d
d) (+)-1 ,1-dimethylethyl [(3-fluoro-3-pyrrolidinyl)methyl]carbamate; To a stirred solution of phenylmethyl 3-[({[(1 ,1- dimethylethyl)oxy]carbonyl}amino)methyl]-3-fluoro-1-pyrrolidinecarboxylate (0.90 g, 2.56 mmole) in MeOH (30 mL) at RT was added Pd(OH)2 (100 mg). After 18 h under H2 (1 atm) with stirring, the reaction contents were filtered through Celite (MeOH) and concentrated under reduced pressure to give the title compound (0.54 g, 98%) as an off- white solid: LC-MS (ES) m/e 219 (M + H)+.

References:

GLAXO GROUP LIMITED WO2006/2047, 2006, A2 Location in patent:Page/Page column 163-164