Ammonium formate → HCID 57685732, compound

HRID 1038068Notes

Reaction equation

HRID 1038068 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([O:18][CH2:19][CH:20]=[CH2:21])[CH2:10][CH2:9][N:8](CC2C=CC=CC=2)[CH2:7]1)=[O:5])[CH3:2].C([O-])=O.[NH4+]>[Pd].CO>[CH2:1]([O:3][C:4]([C:6]1([O:18][CH2:19][CH2:20][CH3:21])[CH2:10][CH2:9][NH:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 57685982HCID 57685982, compound

Product 1

HCID 57685732HCID 57685732, compoundYield 83.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-allyloxy-1-benzyl-pyrrolidine-3-carboxylic acid ethyl ester (145 mg), ammonium formate (126 mg), 10% Pd/C (20 mg) and methanol (4 ml) was refluxed for 40 minutes. The mixture was filtered through Celite, washed with ethyl acetate. The combined filtrate was concentrated and the residue was taken into ethyl acetate, washed with brine and dried over MgSO4. Evaporation of solvent provided the title compound as oil (84 mg).

Workup

  1. temperaturewas refluxed for 40 minutes
  2. filtrationThe mixture was filtered through Celite
  3. washwashed with ethyl acetate
  4. concentrationThe combined filtrate was concentrated
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. customEvaporation of solvent

Sources & evidence

ORD record
ord-33e947dba70540de84f996192b4c1314
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

Loading…