Ethyl 1-benzylpyrrolidine-3-carboxylate → Ethyl pyrrolidine-3-carboxylate

HRID 2293437Notes

Reaction equation

HRID 2293437 reaction equation
C([N:8]1[CH2:12][CH2:11][CH:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9]1)C1C=CC=CC=1>C(O)C.[OH-].[OH-].[Pd+2]>[C:13]([CH:10]1[CH2:11][CH2:12][NH:8][CH2:9]1)([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 1

HCID 11622765Ethyl 1-benzylpyrrolidine-3-carboxylate

Product 1

HCID 12896002Ethyl pyrrolidine-3-carboxylateYield 48.7%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-benzyl-3-carboethoxypyrrolidine (2 g, 8.6 mmol) in ethanol (75 ml) was subjected to hydrogenolysis over Pd(OH)2 on a parr shaker for 48 hr. The catalyst was filtered off, the solvent removed under vacuum, and the residue chromatographed through alumina using dichloromethane/methanol (85:15) as eluant, to give the title product as a clear liquid (0.6 g); δ(60 MHz, CDCl3) 1.20 (3H, t, J=7 Hz, OCH2CH3); 1.70-2.30 (2H, m, CH2); 2.50-3.20 (5H, m, 2×CH2 --N, and CH--CO2Et); 4.10 (2H, q, J=7 Hz, OCH2CH3).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent removed under vacuum
  3. customthe residue chromatographed through alumina

Sources & evidence

ORD record
ord-5b74a5e1ca4f47b0b6a5e22e52b1dfe9
Source dataset
uspto-grants-1997_11
Patent number
US05686463

Reaction notes

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