Citric Acid → 2-(Pyrrolidine-1-carbonyl)-hexahydro-cyclopenta[c]pyrrol-5-one
Reaction equation
[CH2:1]1[CH:5]2[CH2:6][C:7](=[O:9])[CH2:8][CH:4]2[CH2:3][NH:2]1.[N:10]1([C:15](Cl)=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11]1.C(N(CC)CC)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl>[N:10]1([C:15]([N:2]2[CH2:3][CH:4]3[CH2:8][C:7](=[O:9])[CH2:6][CH:5]3[CH2:1]2)=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Hexahydro-cyclopenta[c]pyrrol-5-one triflutate 1f (478 mg, 2 mmol) was dissolved in 20 mL dichloromethane, and pyrrolidine-1-carbonyl chloride (0.276 mL, 2.5 mmol) and triethylamine (0.84 mL, 6 mmol) were then added to the solution in an ice-water bath. Upon completion of the addition, the reaction mixture was stirred overnight at room temperature, 10% citric acid solution was then added to the mixture to adjust to pH 4. The mixture was extracted with dichloromethane (50 mL×3). The combined organic extracts were washed with 50 mL of saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound 2-(pyrrolidine-1-carbonyl)-hexahydro-cyclopenta[c]pyrrol-5-one 8a (0.26 g, yield 58.5%) as a colorless oil.
Workup
- additionUpon completion of the addition
- extractionThe mixture was extracted with dichloromethane (50 mL×3)
- washThe combined organic extracts were washed with 50 mL of saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-75fbdeaf84df46299324d70ebe6fbc01
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08178575B2
Reaction notes
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