Methanol → 2,3-Dihydro-6-methyl-5-(4-methylbenzoyl)-1H-pyrrolizine-1-carboxylic acid

HRID 372228Notes

Reaction equation

HRID 372228 reaction equation
[C:1]1([CH3:24])[CH:6]=[CH:5][C:4]([C:7]([C:9]2[N:13]3[CH2:14][CH2:15][CH:16]([C:17]([O:19]C(C)C)=[O:18])[C:12]3=[CH:11][C:10]=2[CH3:23])=[O:8])=[CH:3][CH:2]=1.CO.C(=O)([O-])[O-].[K+].[K+]>O>[C:1]1([CH3:24])[CH:2]=[CH:3][C:4]([C:7]([C:9]2[N:13]3[CH2:14][CH2:15][CH:16]([C:17]([OH:19])=[O:18])[C:12]3=[CH:11][C:10]=2[CH3:23])=[O:8])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 13780958isopropyl 5-p-toluoyl-1,2-dihydro-6-methyl-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate

Product 1

HCID 137809712,3-Dihydro-6-methyl-5-(4-methylbenzoyl)-1H-pyrrolizine-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 500 mg. of isopropyl 5-p-toluoyl-1,2-dihydro-6-methyl-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate in 15 ml. of methanol is treated with a solution of 1.05 g. of potassium carbonate in 8 ml. of water. The reaction mixture is refluxed under nitrogen atmosphere for 30 minutes, cooled, and evaporated to dryness. The residue is taken up in 10 ml. of 10% aqueous hydrochloric acid and 50 ml. of water and the resultant mixture extracted with ethyl acetate (3 × 50 ml.). The combined extracts are dried over magnesium sulfate and evaporated to dryness under reduced pressure, to give 5-p-toluoyl-1,2-dihydro-6-methyl-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid [(A), R = CH3, R1 = p-CH3 ].

Workup

  1. temperatureThe reaction mixture is refluxed under nitrogen atmosphere for 30 minutes
  2. temperaturecooled
  3. customevaporated to dryness
  4. extractionof water and the resultant mixture extracted with ethyl acetate (3 × 50 ml.)
  5. dry with materialThe combined extracts are dried over magnesium sulfate
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-a122a6e133b541869c32de0eee4a3313
Source dataset
uspto-grants-1978_05
Patent number
US04089969

Reaction notes

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