1-Benzyl 3-methyl pyrrolidine-1,3-dicarboxylate → Methyl Pyrrolidine-3-carboxylate

HRID 1957566Notes

Reaction equation

HRID 1957566 reaction equation
[C:1]([CH:5]1[CH2:9][CH2:8][N:7](C(OCC2C=CC=CC=2)=O)[CH2:6]1)([O:3][CH3:4])=[O:2]>CO.[Pd]>[C:1]([CH:5]1[CH2:9][CH2:8][NH:7][CH2:6]1)([O:3][CH3:4])=[O:2]

Participants

4

Reactant 1

HCID 113460671-Benzyl 3-methyl pyrrolidine-1,3-dicarboxylate

Product 1

HCID 4114360Methyl Pyrrolidine-3-carboxylateYield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4.6 g of benzyl 3-carbomethoxypyrrolidine-1-carboxylate in 150 mL of anhydrous methanol was added 0.92 g of 10% Pd/C. The reaction mixture was placed under an atmosphere of hydrogen and stirred overnight at room temperature. The reaction mixture was then filtered through a Celite® pad, and the filtrate concentrated in vacuo. The residue was chromatographed on silica gel with 2-16% CH3OH/CHCl3 to give 1.40 g (62% yield) of 3-carbomethoxypyrrolidine as a clear oil, 1H NMR (300 MHz, CDCl3) δ1.90-2.10 (m, 2 H); 2.97-3.11 (m, 4H); 3.18-3.29 (m, 2H); 3.44 (s, 3H).

Workup

  1. filtrationThe reaction mixture was then filtered through a Celite® pad
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was chromatographed on silica gel with 2-16% CH3OH/CHCl3

Sources & evidence

ORD record
ord-911cd211ddd54e6aa14d9fdcf5b7c855
Source dataset
uspto-grants-1998_07
Patent number
US05786358

Reaction notes

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