Acetic Acid → Diethyl 3,3-dimethylpyrrolidine-2,2-dicarboxylate

HRID 1439710Notes

Reaction equation

HRID 1439710 reaction equation
C(O[C:9]([NH:11][CH:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=O)C1C=CC=CC=1.[O-]CC.[Na+].[CH3:27][C:28]([CH3:32])=[CH:29]C=O.C(O)(=O)C>C(O)C.[Pd]>[C:18]([C:12]1([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:28]([CH3:32])([CH3:29])[CH2:27][CH2:9][NH:11]1)([O:20][CH2:21][CH3:22])=[O:19]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 610203-Methyl-2-butenalHCID 259787Diethyl 2-(benzyloxycarbonylamino)malonateHCID 2723922Sodium ethoxide

Product 1

HCID 21866189Diethyl 3,3-dimethylpyrrolidine-2,2-dicarboxylateYield 37%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent3×

Procedure

Diethyl benzyloxycarbonylaminomalonate (3.09 g, 10 mM) was dissolved in dry ethanol (15 ml) and added to a solution of sodium ethoxide (from 100 mg sodium) in ethanol (3 ml). 3-Methylbut-2-enal (840 mg, 10 mM) in ethanol (6 ml) was added and the solution stirred at 25° for 24 hrs. Acetic acid (0.28 ml) was then added and the solution hydrogenated for 24 hrs using palladium on carbon (10% 500 mg) as catalyst. The solution was filtered, evaporated and the residue chromatographed on silica column using ether/petroleum ether (40°-60°) (1 : 1) as eluant to give 2,2-dicarboethoxy-3,3-dimethylpyrrolidine (0.9 g).

Workup

  1. waitthe solution hydrogenated for 24 hrs
  2. filtrationThe solution was filtered
  3. customevaporated
  4. customthe residue chromatographed on silica column
  5. customether/petroleum ether (40°-60°) (1 : 1)

Sources & evidence

ORD record
ord-eca233f529344b6385ba0fa825796422
Source dataset
uspto-grants-1977_11
Patent number
US04060603

Reaction notes

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