Potassium Carbonate → 2-Dimethylcarbamoyl-5-methyl-octahydro-cyclopenta[c]pyrrole-5-carboxylic acid
Reaction equation
[CH3:1][N:2]([CH3:16])[C:3]([N:5]1[CH2:9][CH:8]2[CH2:10][C:11](C#N)([CH3:13])[CH2:12][CH:7]2[CH2:6]1)=[O:4].[C:17](=[O:20])([O-])[O-:18].[K+].[K+]>Cl.O>[CH3:1][N:2]([CH3:16])[C:3]([N:5]1[CH2:9][CH:8]2[CH2:10][C:11]([CH3:13])([C:17]([OH:18])=[O:20])[CH2:12][CH:7]2[CH2:6]1)=[O:4]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
5-Cyano-5-methyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 12b (6.99 g, 31.6 mmol) was dissolved in 90 mL of hydrochloric acid (36%). The reaction mixture was heated at 50° C. in an oil bath and stirred for 48 hours. The reaction was monitored by TLC until the disappearance of the starting materials. The reaction mixture was diluted with 100 mL of water. Upon cooling by an ice-water bath, the mixture was adjusted to pH 6 with potassium carbonate and extracted with ethyl acetate (1500 mL×3) and dichloromethane (150 mL×3) successively. The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the title compound 2-dimethylcarbamoyl-5-methyl-octahydro-cyclopenta[c]pyrrole-5-carboxylic acid 12c (7.0 g, yield 92%) as a yellow liquid, which was directly used in the next step.
Workup
- temperatureUpon cooling by an ice-water bath
- extractionextracted with ethyl acetate (1500 mL×3) and dichloromethane (150 mL×3) successively
- dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-180b6c7f410d49f7be07cb8ff1ca99d6
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08304411B2
Reaction notes
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