(S)-2-Cyclobutylcarbamoyl-pyrrolidine-1-carboxylic acid benzyl ester → (2S)-N-cyclobutylpyrrolidine-2-carboxamide

HRID 1970636Notes

Reaction equation

HRID 1970636 reaction equation
C(OC([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=[O:22])[NH:17][CH:18]1[CH2:21][CH2:20][CH2:19]1)=O)C1C=CC=CC=1>C(O)C.[Pd]>[CH:18]1([NH:17][C:16]([C@@H:12]2[CH2:13][CH2:14][CH2:15][NH:11]2)=[O:22])[CH2:21][CH2:20][CH2:19]1

Participants

4

Reactant 1

HCID 66854900(S)-2-Cyclobutylcarbamoyl-pyrrolidine-1-carboxylic acid benzyl ester

Product 1

HCID 62415949(2S)-N-cyclobutylpyrrolidine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 9.00 g (S)-2-Cyclobutylcarbamoyl-pyrrolidine-1-carboxylic acid benzyl ester in 120 ml ethanol were added 1.0 g Pd/C (10%) and the suspension stirred under an atmosphere of hydrogen (3 bar) for 12 h. The reaction mixture was filtrated over a plug of Celite, washed with ethanol and concentrated to give the crude product which was used in the subsequent reaction. Yield: 3.3 g.

Workup

  1. filtrationThe reaction mixture was filtrated over a plug of Celite
  2. washwashed with ethanol
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-12b4bc4050a5477ea0fcb698f7366676
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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