N-[(3aS*,4S*,6aR*)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl]-2,2-dicyclohexylacetamide → 2,2-Dicyclohexyl-N-((3aS,4S,6aR)-octahydrocyclopenta[c]pyrrol-4-yl)acetamide

HRID 2363468Notes

Reaction equation

HRID 2363468 reaction equation
C([N:8]1[CH2:12][C@H:11]2[C@@H:13]([NH:16][C:17](=[O:31])[CH:18]([CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH2:14][CH2:15][C@H:10]2[CH2:9]1)C1C=CC=CC=1>[OH-].[OH-].[Pd+2].CO>[CH:25]1([CH:18]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:17]([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)=[O:31])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1

Participants

4

Reactant 1

HCID 54674167N-[(3aS*,4S*,6aR*)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl]-2,2-dicyclohexylacetamide

Product 1

HCID 462130532,2-Dicyclohexyl-N-((3aS,4S,6aR)-octahydrocyclopenta[c]pyrrol-4-yl)acetamide

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

N-[(3aS,4S,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl]-2,2-dicyclohexylacetamide (2.65 g, 6.27 mmol) from Example 15 and methanol (60 mL) were added to 20% palladium hydroxide on carbon (wet, 0.530 g, 3.77 mmol) in a 250 mL pressure bottle. The reaction was stirred for 16 hours under hydrogen (30 psi) at room temperature. The mixture was filtered through a nylon membrane and the solvent removed in vacuo. The crude material was chromatographed on a silica gel cartridge (Analogix®, Burlington, Wis., RS25-25) eluting with 1-10% methanol (2 N ammonia)/dichloromethane to give the title compound: 1H NMR (500 MHz, pyridine-d5) δ ppm 7.97 (d, J=7.1, 1H), 4.57 (dt, J=7.0, 13.8, 1H), 3.03 (dd, J=3.2, 10.1, 1H), 2.89 (dd, J=7.8, 9.7, 1H), 2.78 (dd, J=7.4, 10.1, 1H), 2.71 (ddd, J=3.2, 7.5, 16.7, 1H), 2.58 (dd, J=3.2, 9.8, 1H), 2.50-2.39 (m, J=8.3, 1H), 1.98-1.89 (m, 3H), 1.89-1.80 (m, 3H), 1.79-1.67 (m, J=6.4, 14.9, 7H), 1.66-1.56 (m, 3H), 1.49-1.36 (m, 2H), 1.36-1.28 (m, 1H), 1.28-1.02 (m, 8H); MS (ESI+) m/z 333 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a nylon membrane
  2. customthe solvent removed in vacuo
  3. customThe crude material was chromatographed on a silica gel cartridge (Analogix®, Burlington, Wis., RS25-25)
  4. washeluting with 1-10% methanol (2 N ammonia)/dichloromethane

Sources & evidence

ORD record
ord-d2dcdfb416d94836a8fadc4ee7f53bc0
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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