Ammonium formate → Methyl 3-(methoxymethyl)pyrrolidine-3-carboxylate

HRID 1038019Notes

Reaction equation

HRID 1038019 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH2:17][O:18][CH3:19])[CH2:9][CH2:8][N:7](CC2C=CC=CC=2)[CH2:6]1)=[O:4].C([O-])=O.[NH4+]>[Pd].CO>[CH3:1][O:2][C:3]([C:5]1([CH2:17][O:18][CH3:19])[CH2:9][CH2:8][NH:7][CH2:6]1)=[O:4]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 59511352Methyl 1-benzyl-3-(methoxymethyl)pyrrolidine-3-carboxylate

Product 1

HCID 59511362Methyl 3-(methoxymethyl)pyrrolidine-3-carboxylateYield 57%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-benzyl-3-methoxymethyl-pyrrolidine-3-carboxylic acid methyl ester (373 mg, 1.42 mmol), ammonium formate (358 mg, 5.68 mmol), 10% Pd/C (100 mg) and methanol (6 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 small amount of water. Aqueous layer was isolated, extracted with dichloromethane three times. The dichloromethane extracts were combined with previous ethyl acetate extracts and dried over MgSO4. Evaporation of solvents provided the title compound as oil (140 mg, 57%).

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 small amount of water
  6. customAqueous layer was isolated
  7. extractionextracted with dichloromethane three times
  8. dry with materialdried over MgSO4
  9. customEvaporation of solvents

Sources & evidence

ORD record
ord-41c704571dfc426ba168a8f00f2e436f
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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