Sodium hydride → Dimethyl 2,3-dihydro-1H-pyrrolizine-1,7-dicarboxylate

HRID 224464Notes

Reaction equation

HRID 224464 reaction equation
I[CH2:2][CH2:3][N:4]1[CH:8]=[CH:7][C:6]([C:9]([O:11][CH3:12])=[O:10])=[C:5]1[CH2:13][C:14]([O:16][CH3:17])=[O:15].[H-].[Na+]>CN(C)C=O>[CH:13]1([C:14]([O:16][CH3:17])=[O:15])[CH2:2][CH2:3][N:4]2[CH:8]=[CH:7][C:6]([C:9]([O:11][CH3:12])=[O:10])=[C:5]12

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 12795009methyl N-(2-iodoethyl)-3-carbomethoxypyrrole-2-acetate

Product 1

HCID 12795063Dimethyl 2,3-dihydro-1H-pyrrolizine-1,7-dicarboxylateYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1 g of methyl N-(2-iodoethyl)-3-carbomethoxypyrrole-2-acetate in 5 ml of dry dimethylformamide is stirred, under an atmosphere of argon, with 137 mg of 50% sodium hydride in mineral oil. The reaction mixture is maintained for 20 minutes at room temperature and then quenched with 100 ml of water. The product is extracted with ethyl acetate (3×50 ml), the combined extracts are washed with water, dried over magnesium sulfate and evaporated to dryness. Chromatography of the residue on 20 g of silica gel using hexane:ethyl acetate (4:1) as eluant, affords 500 mg (80%) of dimethyl 1,2-dihydro-3H-pyrrolo-[1,2-a]pyrrole-1,7-dicarboxylate (VII, R=H) m.p. 70°-71° C.

Workup

  1. customquenched with 100 ml of water
  2. extractionThe product is extracted with ethyl acetate (3×50 ml)
  3. washthe combined extracts are washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-3cf28d9de3c24b68bf3efc97f516a810
Source dataset
uspto-grants-1980_11
Patent number
US04232038

Reaction notes

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