Hydrochloric Acid → 2-(2,6-Dimethylphenyl)-1-oxooctahydrocyclopenta[c]pyrrole-3a-carboxylic acid

HRID 1021002Notes

Reaction equation

HRID 1021002 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]1[CH2:13][C:12]2([C:17]([O:19]C)=[O:18])[CH2:14][CH2:15][CH2:16][CH:11]2[C:10]1=[O:21].Cl>[Li+].[OH-].CO.O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]1[CH2:13][C:12]2([C:17]([OH:19])=[O:18])[CH2:14][CH2:15][CH2:16][CH:11]2[C:10]1=[O:21]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 58218817Methyl 2-(2,6-dimethylphenyl)-1-oxooctahydrocyclopenta[c]pyrrole-3a-carboxylate

Product 1

HCID 582187902-(2,6-Dimethylphenyl)-1-oxooctahydrocyclopenta[c]pyrrole-3a-carboxylic acidYield 82.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 3939Lithium HydroxideSolvent

Conditions

Temperature
70 °C

Procedure

Methyl 2-(2,6-dimethylphenyl)-1-oxooctahydrocyclopenta[c]pyrrole-3a-carboxylate (400 mg, 1.4 mmol) suspended in 5 mL of 1 M LiOH in 90% methanol was heated at 70° C. After cooling to room temperature, the reaction mixture was diluted with water, the pH adjusted to ˜1 with concentrated HCl and the product was extracted twice with ethyl acetate (15 mL). The combined organic layer was dried over anhydrous Na2SO4 and the solvent was evaporated to yield 2-(2,6-dimethylphenyl)-1-oxooctahydrocyclopenta[c]pyrrole-3a-carboxylic acid (315 mg, 82% yield). LC-MS Rt (retention time): 1.44 min, MS: (ES) m/z 274 (M+H+).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe product was extracted twice with ethyl acetate (15 mL)
  3. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-fc405867031c4481bc385fed17c60c1d
Source dataset
uspto-grants-2014_05
Patent number
US08716494B2

Reaction notes

Loading…