1-Benzyl-3-aminopyrrolidine → HCID 57874467, compound

HRID 1093836Notes

Reaction equation

HRID 1093836 reaction equation
[O:1]=[C:2]([N:24]1[CH2:29][CH2:28][CH:27]([O:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[CH:32]=2)[CH2:26][CH2:25]1)[CH2:3][NH:4][C:5]([C:7]1[N:8]=[N:9][N:10]([CH:12]2[CH2:16][CH2:15][N:14](CC3C=CC=CC=3)[CH2:13]2)[CH:11]=1)=[O:6].C(N1CCC(N)C1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[O:1]=[C:2]([N:24]1[CH2:29][CH2:28][CH:27]([O:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:38])([F:39])[F:40])[CH:32]=2)[CH2:26][CH2:25]1)[CH2:3][NH:4][C:5]([C:7]1[N:8]=[N:9][N:10]([CH:12]2[CH2:16][CH2:15][NH:14][CH2:13]2)[CH:11]=1)=[O:6]

Participants

5

Reactant 2

HCID 27566131-Benzyl-3-aminopyrrolidineHCID 66592268HCID 66592268, compound

Product 1

HCID 57874467HCID 57874467, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Pd(OH)2 (80 mg) was added to a stirred solution of 1-(1-benzyl-pyrrolidin-3-yl)-1H-[1,2,3]triazole-4-carboxylic acid {2-oxo-2-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide (prepared by the method used for the synthesis of Example 136, starting from 1-benzyl-3-aminopyrrolidine) (407 mg, 0.73 mmol) in MeOH (4 mL) in an inert atmosphere and stirring was continued under H2 gas atmosphere for 6 hrs. The reaction mixture was filtered through celite. The filtrate collected was concentrated under reduced pressure to afford 260 mg (80.2% Yield) of 1-pyrrolidin-3-yl-1H-[1,2,3]triazole-4-carboxylic acid {2-oxo-2-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide. LC/MS [M+H]+: 467.19.

Workup

  1. customprepared by the method
  2. customused for the synthesis of Example 136
  3. filtrationThe reaction mixture was filtered through celite
  4. customThe filtrate collected
  5. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-b9aaff3ed02742b5b21c84efd07b0a00
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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