Methyl iodide → 1-Benzyl 3-methyl pyrrolidine-1,3-dicarboxylate

HRID 1034955Notes

Reaction equation

HRID 1034955 reaction equation
[C:1]([N:11]1[CH2:15][CH2:14][CH:13]([C:16]([OH:18])=[O:17])[CH2:12]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].IC.[C:21](=O)([O-])O.[K+]>CN(C=O)C>[CH3:21][O:17][C:16]([CH:13]1[CH2:14][CH2:15][N:11]([C:1]([O:3][CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:2])[CH2:12]1)=[O:18]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 516893Potassium BicarbonateHCID 185384831-N-Cbz-pyrrolidine-3-carboxylic acid

Product 1

HCID 113460671-Benzyl 3-methyl pyrrolidine-1,3-dicarboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-carbobenzyloxypyrrolidine-3-carboxylic acid (10.15 g, 40.72 mmol) and iodomethane (5.08 mL, 81.44 mmol) in N,N′-dimethylformamide (80 mL) was added powdered potassium hydrogen carbonate (8.15 g, 81.44 mmol) and the reaction mixture stirred at ambient temperature for 5 hours. The mixture was partitioned between ethyl acetate and brine and the organic phase washed with water and concentrated. The residue was purified by flash chromatography on silica gel using 5-50% ethyl acetate in hexane to give the title compound (10.59 g, 99%). MS(DCI): m/z 264 (M+H)+.

Workup

  1. customThe mixture was partitioned between ethyl acetate and brine
  2. washthe organic phase washed with water
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography on silica gel using 5-50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-08d32483e4d8436abb97614f421d439c
Source dataset
uspto-grants-2013_10
Patent number
US08546368B2

Reaction notes

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