Tert-butyl-3-(2-ethoxy-2-oxoethylidene)pyrrolidine-1-carboxylate → tert-Butyl 3-(2-ethoxy-2-oxoethyl)pyrrolidine-1-carboxylate

HRID 1253523Notes

Reaction equation

HRID 1253523 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH:5]=[C:6]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7]1)[CH3:2]>[Pd].CCO>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH:6]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7]1)[CH3:2]

Participants

4

Reactant 1

HCID 67205087Tert-butyl-3-(2-ethoxy-2-oxoethylidene)pyrrolidine-1-carboxylate

Product 1

HCID 15384752tert-Butyl 3-(2-ethoxy-2-oxoethyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A flask was charged with EtOH (700 ml), tert-butyl 3-(2-ethoxy-2-oxoethylidene)pyrrolidine-1-carboxylate (246 g, 965 mmol) and Pd/C (40 g). Then the flask was charged with H2 (3 L). The resulting solution was stirred overnight. The reaction mixture was filtered and concentrated to afford tert-butyl 3-(2-ethoxy-2-oxoethyl)pyrrolidine-1-carboxylate as a colorless oil.

Workup

  1. additionThen the flask was charged with H2 (3 L)
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4ab1f571054840fe81fa465cae412560
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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