Hydrochloric Acid → 2,3-Dihydro-1H-pyrrolizine-1,7-dicarboxylic acid

HRID 2352041Notes

Reaction equation

HRID 2352041 reaction equation
[CH:1]1([C:13]([O:15]C)=[O:14])[CH2:5][CH2:4][N:3]2[CH:6]=[CH:7][C:8]([C:9]([O:11]C)=[O:10])=[C:2]12.[OH-].[Na+].Cl>O>[CH:8]1([C:9]([OH:11])=[O:10])[CH2:7][CH2:6][N:3]2[CH:4]=[CH:5][C:1]([C:13]([OH:15])=[O:14])=[C:2]12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12795063Dimethyl 2,3-dihydro-1H-pyrrolizine-1,7-dicarboxylate

Product 1

HCID 127950822,3-Dihydro-1H-pyrrolizine-1,7-dicarboxylic acidYield 71.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Dimethyl 2,3-dihydro-1H-pyrrolo[1,2-a]pyrrole-1,7-dicarboxylate (1.26 g, 5 mmol) and sodium hydroxide (1.00 g, 25 mmol) were heated in water (10 mL) at reflux for 1 hour. The resulting solution was cooled to 0° C. and acidified with hydrochloric acid (12 M) to pH 1. 2,3-Dihydro-1H-pyrrolo-[1,2-a]pyrrole-1,7-dicarboxylic acid (0.70 g, 71.4% yield) was collected by filtration and dried.

Workup

  1. temperatureat reflux for 1 hour

Sources & evidence

ORD record
ord-43b654aa488a4251af076a0ccdb79b90
Source dataset
uspto-grants-1989_10
Patent number
US04874872

Reaction notes

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