Potassium Acetate → Tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(pyridin-3-yl)methyl]-5-[4-(methoxycarbonyl)benzyl]pyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(6-chloropyridin-3-yl)methyl]-5-[4-(methoxycarbonyl)benzyl]pyrrolidine-1-carboxylate from Step C (14.0 g, 24.3 mmol) in ethanol (200 mL) was added potassium acetate (3.58, 36.5 mmol) and 10% palladium on carbon (4.0 g) under argon. The reaction mixture was heated to 50° C. and agitated under an atmosphere of hydrogen at 50 psi for 14 h. The mixture was cooled to RT and filtered. The filtrate was concentrated to afford 12.1 g (92%) of the title compound as yellow foam. 1H NMR (400 MHz, CDCl3): δ 8.62 (s, 1H), 8.58 (s, 1H), 7.89 (d, J=7.9 Hz, 2H), 7.36-7.32 (m, 1H), 7.02-6.99 (m, 2H), 5.62 (s, 1H), 4.20-4.11 (m, 2H), 3.94 (s, 3H), 2.99-2.96 (m, 1H), 2.64-2.60 (m, 1H), 2.02-1.88 (m, 2H), 1.61 (s, 9H), 1.56-1.43 (m, 2H), 0.96 (s, 9H), 0.17 (s, 3H), 0.00 (s, 3H). MS: m/z (ESI) 541 (M+1).

Provenance & Evidence