N-[(3aS*,4S*,6aR*)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl]-N-cyclopropyl-3-(trifluoromethyl)benzenesulfonamide → N-cyclopropyl-N-[(3aS*,4S*,6aR*)-octahydrocyclopenta[c]pyrrol-4-yl]-3-(trifluoromethyl)benzenesulfonamide

HRID 2363529Notes

Reaction equation

HRID 2363529 reaction equation
C([N:8]1[CH2:12][C@H:11]2[C@@H:13]([N:16]([CH:30]3[CH2:32][CH2:31]3)[S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)(=[O:19])=[O:18])[CH2:14][CH2:15][C@H:10]2[CH2:9]1)C1C=CC=CC=1>[OH-].[OH-].[Pd+2].CO>[CH:30]1([N:16]([C@@H:13]2[C@H:11]3[C@H:10]([CH2:9][NH:8][CH2:12]3)[CH2:15][CH2:14]2)[S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:28])([F:27])[F:29])[CH:21]=2)(=[O:18])=[O:19])[CH2:31][CH2:32]1

Participants

4

Reactant 1

HCID 68413617N-[(3aS*,4S*,6aR*)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl]-N-cyclopropyl-3-(trifluoromethyl)benzenesulfonamide

Product 1

HCID 66590637N-cyclopropyl-N-[(3aS*,4S*,6aR*)-octahydrocyclopenta[c]pyrrol-4-yl]-3-(trifluoromethyl)benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

(3aS*,4S*,6aR*)-2-benzyl-N-cyclopropyloctahydrocyclopenta[c]pyrrol-4-amine (0.308 g, 0.663 mmol) from Example 199 and methanol (2 mL) were added to 20% palladium hydroxide on carbon (wet, 4 mg) in a 50 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., RS15-24) eluting with 1-10% methanol (2 N ammonia)/dichloromethane to give the title compound: 1H NMR (300 MHz, CDCl3) δ ppm 8.14 (s, 1H), 8.07 (d, J=7.9, 1H), 7.87 (d, J=7.9, 1H), 7.70 (t, J=7.8, 1H), 3.80-3.69 (m, 1H), 3.25 (dd, J=7.8, 10.7, 1H), 3.06-2.88 (m, 2H), 2.79-2.71 (m, 1H), 2.63-2.51 (m, 1H), 2.46 (dd, J=5.9, 10.8, 1H), 2.05 (qd, J=7.0, 12.1, 1H), 1.79 (ddd, J=3.9, 6.8, 10.7, 1H), 1.72-1.63 (m, 2H), 1.56 (dd, J=4.8, 6.1, 1H), 1.48 (td, J=6.9, 12.8, 1H), 1.31 (ddd, J=2.7, 5.5, 8.8, 1H), 0.92-0.70 (m, 3H); MS (ESI+) m/z 375 (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., RS15-24)
  4. washeluting with 1-10% methanol (2 N ammonia)/dichloromethane

Sources & evidence

ORD record
ord-34cf508ec5d24561ba9ba943ddb34412
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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