4-Methyl-3-oxo-1-(phenylmethyl)proline ethyl ester → 1-Benzyl-4-methylpyrrolidin-3-one
Reaction equation
C(OC([CH:6]1[C:10](=[O:11])[CH:9]([CH3:12])[CH2:8][N:7]1[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O)C>Cl>[CH2:13]([N:7]1[CH2:8][CH:9]([CH3:12])[C:10](=[O:11])[CH2:6]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A 30.15 g (115.4 mmol) sample of the ester from step c was hydrolyzed and decarboxylated by adding to 280 mL of 1M HCl and heating at 100° C. under reflux conditions for 12 hours. The mixture was then poured over ice and the impurities extracted into methylene chloride. The aqueous solution was then adjusted to pH 8 with potassium carbonate and the product extracted into methylene chloride, which was then dried over anhydrous sodium sulfate. The solvent was removed by evaporation under vacuum, to yield 9.95 g of 1-benzyl-4-methylpyrrolidin-3-one, NMR (CDCl3) d 1.12 (d, 3H, J=7.5 Hz), 2.50 (m, 1H), 2.75 (m, 2H), 3.33 (m, 2H), 3.69 (d, 2H, J=7.5 Hz), 7.32 (m, 5H).
Workup
- additionThe mixture was then poured over ice
- extractionthe impurities extracted into methylene chloride
- extractionthe product extracted into methylene chloride, which
- dry with materialwas then dried over anhydrous sodium sulfate
- customThe solvent was removed by evaporation under vacuum
Sources & evidence
- ORD record
- ord-cc6d2c82379645ea91639be810597d74
- Source dataset
- uspto-grants-1992_08
- Patent number
- US05137892
Reaction notes
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