HCID 54674031, compound → HCID 54674182, compound

HRID 2402741Notes

Reaction equation

HRID 2402741 reaction equation
C([N:8]1[CH2:12][C@@H:11]2[C@@:13]([NH:17][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)([CH3:16])[CH2:14][CH2:15][C@@H:10]2[CH2:9]1)C1C=CC=CC=1.[H][H]>C(O)C(F)(F)F>[CH3:16][C@:13]1([NH:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@@H:11]2[C@@H:10]([CH2:9][NH:8][CH2:12]2)[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 54674031HCID 54674031, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54674182HCID 54674182, compound

Reagents, catalysts & solvents 1

HCID 64092,2,2-TrifluoroethanolSolvent

Procedure

N-[(3aR,4R,6aS)-2-benzyl-4-methyloctahydrocyclopenta[c]pyrrol-4-yl]benzamide from Example 2 (250 mg, 0.747 mmol) and trifluoroethanol (10 mL) were added to 20% Pd(OH)2—C, wet (50.0 mg, 0.356 mmol) in a 50 mL pressure bottle and stirred for 2 hours under 30 psi hydrogen gas at 50° C. The mixture was filtered through a nylon membrane and the solvent removed in vacuo to give the title compound as a white solid: 1H NMR (500 MHz, pyridine-d5) δ ppm 9.40 (s, 1H), 8.22-8.15 (m, 2H), 7.46-7.38 (m, 3H), 3.15 (dd, J=10.2, 1.3, 1H), 2.91-2.86 (m, 1H), 2.83-2.77 (m, 1H), 2.75-2.66 (m, 2H), 2.54 (qd, J=9.1, 2.0, 1H), 2.38 (dd, J=11.8, 4.4, 1H), 1.92-1.84 (m, 1H), 1.75 (s, 3H), 1.49-1.41 (m, 1H), 1.32 (ddt, J=13.0, 10.5, 6.6, 1H); MS (ESI+) m/z 245 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-81eb4fd88a834569be2a7d0f4b02f0f4
Source dataset
uspto-grants-2014_08
Patent number
US08796470B2

Reaction notes

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