HCID 66997255, compound → HCID 66997026, compound

Participants

Reaction Steps

To a solution of (2S,4R)-tert-butyl 2-((3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-ylcarbamoyl)-4-fluoropyrrolidine-1-carboxylate (4.59 g, 10.64 mmol) from Step 1 in ethanol (45 mL) was added to 20% Pd(OH)2—C, wet (0.918 g, 6.54 mmol) in a 250 mL stainless steel pressure bottle. The mixture was shaken under 30 psi of hydrogen at 50° C. for 45 minutes. The mixture was filtered through a nylon membrane and the solvent removed in vacuo to give (2S,4R)-tert-butyl 4-fluoro-2-((3aR,4S,6aS)-octahydrocyclopenta[c]pyrrol-4-ylcarbamoyl)pyrrolidine-1-carboxylate: 1H NMR (400 MHz, pyridine-d5, 90° C.) δ ppm 7.87 (s, 1H), 5.21 (dd, J=53.6, 3.0, 1H), 4.61 (t, J=7.8, 1H), 4.24-4.14 (m, 1H), 3.91 (dd, J=11.6, 3.1, 2H), 3.66 (ddd, J=34.5, 12.8, 3.6, 1H), 3.15-3.05 (m, 2H), 2.96 (dd, J=10.7, 7.3, 1H), 2.68 (dd, J=10.7, 3.7, 1H), 2.64-2.57 (m, 1H), 2.57-2.31 (m, 3H), 2.10-2.00 (m, 1H), 1.95-1.85 (m, 1H), 1.70-1.58 (m, 1H), 1.49 (s, 9H), 1.41-1.30 (m, 1H); MS (ESI+) m/z 342 (M+H)+.

Provenance & Evidence