HCID 89449684, compound → HCID 131730521, compound

HRID 1969890Notes

Reaction equation

HRID 1969890 reaction equation
C([N:8]1[CH2:12][C@H:11]([CH2:13][CH3:14])[C@H:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:9]1)C1C=CC=CC=1>CCO>[CH2:13]([C@H:11]1[CH2:12][NH:8][CH2:9][C@H:10]1[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:14]

Participants

3

Reactant 1

HCID 89449684HCID 89449684, compound

Product 1

HCID 131730521HCID 131730521, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A parr shaker was charged with PdOH2 on carbon (2.243 g, 3.19 mmol) and (cis)-ethyl 1-benzyl-4-ethylpyrrolidine-3-carboxylate (16.7 g, 63.9 mmol) followed by EtOH (100 mL). The reaction mixture was degassed and purged with hydrogen gas and shaken on the parr shaker at 60 psi for about 4 days at ambient temperature. The reaction mixture was degassed and purged with nitrogen. The suspension was filtered through a pad of Celite® washing with EtOH (˜900 mL). The solvent was removed under reduced pressure to afford (cis)-ethyl 4-ethylpyrrolidine-3-carboxylate (8.69 g, 79%) as an oil: LC/MS (Table 1, Method a) Rt=1.11 min; MS m/z: 172 (M+H)+.

Workup

  1. customThe reaction mixture was degassed
  2. custompurged with hydrogen gas
  3. customThe reaction mixture was degassed
  4. custompurged with nitrogen
  5. filtrationThe suspension was filtered through a pad of Celite®
  6. washwashing with EtOH (˜900 mL)
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8c1db0c2a42a41fc90553b10dc3e23b3
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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