(R)-N-(2-((1-benzylpyrrolidin-3-yl)amino)-2-oxoethyl)-3-(trifluoromethyl)benzamide → (R)-N-(2-oxo-2-(pyrrolidin-3-ylamino)ethyl)-3-(trifluoromethyl)benzamide

HRID 1015991Notes

Reaction equation

HRID 1015991 reaction equation
C([N:8]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:14](=[O:29])[CH2:15][NH:16][C:17](=[O:28])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[CH2:9]1)C1C=CC=CC=1>CO.[OH-].[Pd+2].[OH-]>[NH:8]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:14]([CH2:15][NH:16][C:17](=[O:28])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:25])[F:26])[CH:19]=2)=[O:29])[CH2:9]1

Participants

4

Reactant 1

HCID 44453592(R)-N-(2-((1-benzylpyrrolidin-3-yl)amino)-2-oxoethyl)-3-(trifluoromethyl)benzamide

Product 1

HCID 59556069(R)-N-(2-oxo-2-(pyrrolidin-3-ylamino)ethyl)-3-(trifluoromethyl)benzamide

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a Parr shaker flask containing compound of step B (14.0 g, 34.5 mmol) dissolved in MeOH (50 mL) was added Palladium hydroxide (2.8 g, 20 wt %). The suspension was shaken at rt under hydrogen (55 psi) overnight. The mixture was filtered through celite and concentrated to give the title compound as a white solid; yield 10.5 g, 97%; 1H NMR (CDCl3) δ 9.06 (t, 1H), 8.20 (m, 3H), 7.94 (d, 1H), 7.75 (t, 1H), 4.23 (m, 1H), 3.89 (d, 2H), 3.00-3.22 (m, 4H), 2.82 (m, 1H), 2.05 (m, 1H), 1.73 (m, 1H); MS m/z=316.3 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-c8bb5615f80e45ab81c5f71cc5bcdf24
Source dataset
uspto-grants-2011_07
Patent number
US07985730B2

Reaction notes

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