Potassium Hydroxide → 5-(4-Fluorobenzoyl)-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid

HRID 1462051Notes

Reaction equation

HRID 1462051 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]([C:6]([C:8]2[N:12]3[CH2:13][CH2:14][C:15](C(OC)=O)([C:16]([O:18]C)=[O:17])[C:11]3=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.FC1C=CC(C(C2N3CCC(C(OC)=O)C3=CC=2)=O)=CC=1.[OH-].[K+]>CO.O>[F:1][C:2]1[CH:25]=[CH:24][C:5]([C:6]([C:8]2[N:12]3[CH2:13][CH2:14][CH:15]([C:16]([OH:18])=[O:17])[C:11]3=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 12915912dimethyl 5-(4-fluorobenzoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1,1-dicarboxylateHCID 12915913methyl 5-(4-fluorobenzoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate

Product 1

HCID 129159145-(4-Fluorobenzoyl)-2,3-dihydro-1H-pyrrolizine-1-carboxylic acidYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of the mixture of dimethyl 5-(4-fluorobenzoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1,1-dicarboxylate and methyl 5-(4-fluorobenzoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate (0.200 g) in methanol (5 ml) and water (3 ml) containing potassium hydroxide (0.5 g) was heated at reflux temperature for 1 hour. The solvent was removed in vacuo, water was added to the residue and the solution was made acidic with 10% hydrochloric acid solution. The product was extracted into ethyl acetate, the extract was dried and evaporated. The solid residue on crystallization from ethyl acetate-hexane gave 5-(4-fluorobenzoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid (0.124 g, 80%) m.p. 163°. A mixed m.p. with an authentic specimen (m.p. 170°) had m.p. 165°. The IR spectrum was identical to that of the authentic sample.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 1 hour
  3. customThe solvent was removed in vacuo, water
  4. additionwas added to the residue
  5. extractionThe product was extracted into ethyl acetate
  6. customthe extract was dried
  7. customevaporated
  8. customThe solid residue on crystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-3bf9e5ff3b3e420ab4515076f6b77e76
Source dataset
uspto-grants-1984_07
Patent number
US04458081

Reaction notes

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