(3aR,5R,6aR)-Methyl 2-benzyl-5-((tert-butoxycarbonyl)amino)octahydro-cyclopenta[c]pyrrole-3a-carboxylate → rac-methyl (3aR,5R,6aR)-5-(((tert-butoxy)carbonyl)amino)-octahydrocyclopenta(c)pyrrole-3a-carboxylate

Participants

Reaction Steps

To a solution of the product from Step C (28.6 g, 76.4 mmol) in methanol (200 mL) was added 5% palladium hydroxide on carbon (0.26 g). Hydrogenation proceeded overnight in Parr shaker at rt at 50 psi. Filtration and evaporation to dryness gave the product as a yellow gel. 1H-NMR (400 MHz, CDCl3): δ 1.44 (s, 9H), 1.72-1.90 (m, 2H), 1.93-2.05 (m, 1H), 2.05-2.17 (m, 1H), 2.67 (dd, J=11.6, 5.8 Hz, 1H), 2.77 (d, J=12.1 Hz, 1H), 2.82-2.94 (m, 1H), 3.30 (dd, J=11.6, 8.1 Hz, 1H), 3.44-3.57 (m, 2H), 3.68-3.79 (m, 3H), 4.14 (d, J=6.3 Hz, 1H), 4.85 (d, J=5.8 Hz, 1H). LC/MS: C14H24N2O4: m/z 285.2 (M+H).

Provenance & Evidence