HCID 66997255, compound → HCID 66997026, compound

HRID 2363630Notes

Reaction equation

HRID 2363630 reaction equation
C([N:8]1[CH2:12][C@@H:11]2[C@@H:13]([NH:16][C:17]([C@@H:19]3[CH2:23][C@@H:22]([F:24])[CH2:21][N:20]3[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[O:18])[CH2:14][CH2:15][C@@H:10]2[CH2:9]1)C1C=CC=CC=1.[H][H]>C(O)C>[F:24][C@H:22]1[CH2:21][N:20]([C:25]([O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:26])[C@H:19]([C:17](=[O:18])[NH:16][C@@H:13]2[C@@H:11]3[C@@H:10]([CH2:9][NH:8][CH2:12]3)[CH2:15][CH2:14]2)[CH2:23]1

Participants

4

Reactant 2

HCID 66997255HCID 66997255, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66997026HCID 66997026, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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)+.

Workup

  1. filtrationThe mixture was filtered through a nylon membrane
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-df8d1565f3764326bd9bca9df3490c2b
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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