Ammonium formate → Rac-2-(3,5-bis-trifluoromethyl-phenyl)-n-methyl-n-((3s,4r)-4-phenyl-pyrrolidin-3-yl)-isobutyramide

HRID 1365906Notes

Reaction equation

HRID 1365906 reaction equation
C([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@H:10]([N:19]([CH3:39])[C:20](=[O:38])[C:21]([C:24]2[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[C:26]([C:34]([F:37])([F:36])[F:35])[CH:25]=2)([CH3:23])[CH3:22])[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[F:32][C:30]([F:31])([F:33])[C:28]1[CH:29]=[C:24]([C:21]([CH3:22])([CH3:23])[C:20]([N:19]([CH3:39])[C@H:10]2[C@H:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:12][NH:8][CH2:9]2)=[O:38])[CH:25]=[C:26]([C:34]([F:35])([F:36])[F:37])[CH:27]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 87211937Rac-n-((3s,4r)-1-benzyl-4-phenyl-pyrrolidin-3-yl)-2-(3,5-bis-trifluoromethyl-phenyl)-n-methyl-isobutyramide

Product 1

HCID 59840126Rac-2-(3,5-bis-trifluoromethyl-phenyl)-n-methyl-n-((3s,4r)-4-phenyl-pyrrolidin-3-yl)-isobutyramideYield 104.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of rac-N-((3S,4R)-1-Benzyl-4-phenyl-pyrrolidin-3-yl)-2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-isobutyramide (1.0 g, 1.82 mmol) in MeOH (30 ml) was added ammonium formate (0.59 g, 9.3 mmol) and Pd/C 10% (0.25 g). Stirring was continued at RT for 1 h, the reaction mixture was then filtered through celite, concentrated under vacuo. Purification by flash chromatography (SiO2, CH2Cl2/MeOH 8:2) yielded 0.87 g (84%) of rac-2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-N-((3S,4R)-4-phenyl-pyrrolidin-3-yl)-isobutyramide as a colorless oil. ES-MS m/e: 459.4 (M+H+).

Workup

  1. filtrationthe reaction mixture was then filtered through celite
  2. concentrationconcentrated under vacuo
  3. customPurification by flash chromatography (SiO2, CH2Cl2/MeOH 8:2)

Sources & evidence

ORD record
ord-2dfe86e28c1d43fda2cd7466b65b9dab
Source dataset
uspto-grants-2011_02
Patent number
US07893062B2

Reaction notes

Loading…