Ammonium formate → HCID 131728355, compound

HRID 1038014Notes

Reaction equation

HRID 1038014 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:18]([CH3:26])([CH3:25])[O:19][SiH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:10][CH2:9][N:8](CC2C=CC=CC=2)[CH2:7]1)=[O:5])[CH3:2].C([O-])=O.[NH4+]>CO.O.[Pd]>[CH2:1]([O:3][C:4]([C:6]1([C:18]([CH3:25])([CH3:26])[O:19][SiH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:10][CH2:9][NH:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 131728353HCID 131728353, compound

Product 1

HCID 131728355HCID 131728355, compoundYield 84.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 1-benzyl-3-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidine-3-carboxylic acid ethyl ester (690 mg, 1.83 mmol), ammonium formate (461 mg, 7.31 mmol), 10% Pd/C (100 mg) in methanol (10 ml) and water (1 ml) was refluxed overnight. 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 (444 mg, 84%).

Workup

  1. temperaturewas refluxed overnight
  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-4539ab53be6b4816b65adbb82ee0e9d9
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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