Ammonium formate → Methyl Pyrrolidine-3-carboxylate

HRID 1767134Notes

Reaction equation

HRID 1767134 reaction equation
C([O-])=O.[NH4+].C1(C[N:12]2[CH2:16][CH2:15][CH:14]([C:17]([O:19][CH3:20])=[O:18])[CH2:13]2)C=CC=CC=1>[Pd].CO>[NH:12]1[CH2:16][CH2:15][CH:14]([C:17]([O:19][CH3:20])=[O:18])[CH2:13]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 4610751Methyl 1-benzylpyrrolidine-3-carboxylate

Product 1

HCID 4114360Methyl Pyrrolidine-3-carboxylateYield 84.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.704 g of 10% palladium on carbon (Pd/C) and then 11.5 g of ammonium formate are successively added at a temperature in the region of 20° C., under an argon atmosphere, to 5 g (22.8 mmol) of methyl (±)-1-(phenylmethyl)-3-pyrrolidinecarboxylate in solution in 100 cm3 of methanol. After stirring for 3 hours at the reflux temperature, the reaction mixture is filtered on Celite®. The Celite® is rinsed with 3 times 20 cm3 of methanol. The filtrate is then concentrated to dryness under reduced pressure (2.7 kPa) to give 2.5 g of methyl (±)-3-pyrrolidinecarboxylate in the form of a colorless oil.

Workup

  1. filtrationthe reaction mixture is filtered on Celite®
  2. washThe Celite® is rinsed with 3 times 20 cm3 of methanol
  3. concentrationThe filtrate is then concentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-6762458bf2e742619342ec2c7716cc58
Source dataset
uspto-grants-2007_06
Patent number
US07232833B2

Reaction notes

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