Acetic Acid → diethyl 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylate

HRID 1090847Notes

Reaction equation

HRID 1090847 reaction equation
C(O)(=O)C.C(#N)C.C([O-])(=O)C.[Na+].[C:13]([C:21]1[NH:22][CH:23]=[CH:24][C:25]=1[CH2:26][CH2:27][CH:28]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:29]([O:31][CH2:32][CH3:33])=[O:30])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(OCC)C.[Mn+3].C([O-])(=O)C.[Mn+3].C([O-])(=O)C.C([O-])(=O)C>[C:13]([C:21]1[N:22]2[C:27](=[CH:26][CH:25]=1)[C:28]([C:34]([O:36][CH2:37][CH3:38])=[O:35])([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:24][CH2:23]2)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 6342AcetonitrileHCID 517045Sodium AcetateHCID 53958697HCID 53958697, compound

Product 1

HCID 9928574diethyl 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylate

Reagents, catalysts & solvents 3

HCID 105130Manganese(3+)CatalystHCID 160554manganese(III) acetate dihydrateCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a warm, preferably 60°-80° C., mixture of a high valence metal ion, preferably a manganese(III) salt, and more preferably manganese(III) acetate, in an alkanoic acid, preferably acetic acid, or a polar aprotic solvent such as acetonitrile, is added a weak base, preferably sodium acetate, and a compound of formula IV, preferably 2-benzoyl-[3,3-di(ethoxycarbonyl)propyl]pyrrole. The reaction is stirred, preferably at 50°-70° C. until the reaction is complete. The reaction mixture is diluted with a polar solvent, such as diethyl ether, and filtered. The resulting solution is washed with water and aqueous base, preferably 10% sodium hydroxide, dried, and concentrated under reduced pressure. The product, a compound of formula I, preferably diethyl 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylate, may be isolated by conventional means.

Workup

  1. additionTo a warm, preferably 60°-80° C., mixture of a high valence metal ion
  2. filtrationfiltered
  3. washThe resulting solution is washed with water and aqueous base, preferably 10% sodium hydroxide
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-87d775facd59459db77d8e10155f09cf
Source dataset
uspto-grants-1992_01
Patent number
US05082951

Reaction notes

Loading…