Ammonium formate → HCID 46901321, compound

HRID 1630276Notes

Reaction equation

HRID 1630276 reaction equation
Cl[C:2]1[S:6][C:5]([CH2:7][C@H:8]2[CH2:12][NH:11][C@H:10]([C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=4)=[CH:18][CH:17]=3)=[O:14])[CH2:9]2)=[CH:4][CH:3]=1.C([O-])=O.[NH4+]>[Pd].CO>[F:29][C:26]1[CH:25]=[CH:24][C:23]([O:22][C:19]2[CH:18]=[CH:17][C:16]([NH:15][C:13]([C@@H:10]3[CH2:9][C@@H:8]([CH2:7][C:5]4[S:6][CH:2]=[CH:3][CH:4]=4)[CH2:12][NH:11]3)=[O:14])=[CH:21][CH:20]=2)=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 46901320HCID 46901320, compound

Product 1

HCID 46901321HCID 46901321, compoundYield 73.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A flask was charged with (2S,4S)-4-((5-chlorothien-2-yl)methyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (340 mg, 0.861 mmol), prepared as in Reference 6, palladium on carbon (10%, 50 mg), ammonium formate (200 mg, 3.33 mmol) and methanol (10 mL) and the mixture was heated to 80° C. The mixture was stirred at 80° C. for 30 minutes, filtered and then concentrated to give crude (2S,4S)—N-(4-(4-fluorophenoxy)phenyl)-4-(thien-2-ylmethyl)pyrrolidine-2-carboxamide (0.252 mg, 0.636 mmol), which was carried forward without further purification.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-a7d5eb256c5a421a952fe29a40cf0e40
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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