Dichloromethane → 2-(Piperidine-1-carbonyl)-hexahydro-cyclopenta[c]pyrrol-5-one
Reaction equation
FC(F)(F)[C:3]([OH:5])=O.[CH2:8]1[CH:12]2[CH2:13][C:14](=[O:16])[CH2:15][CH:11]2[CH2:10][NH:9]1.C([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])C.Cl[CH2:25]Cl>>[N:19]1([C:3]([N:9]2[CH2:10][CH:11]3[CH2:15][C:14](=[O:16])[CH2:13][CH:12]3[CH2:8]2)=[O:5])[CH2:20][CH2:21][CH2:25][CH2:23][CH2:22]1Participants
Procedure
Hexahydro-cyclopenta[c]pyrrol-5-one trifluoroacetate 1f (478 mg, 2 mmol) was dissolved in 20 mL of dichloromethane with stirring followed by addition of ido[3-(1-piperidine-formyl)imidazole-1-methyl] (0.96 g, 3 mmol) and triethylamine (0.84 mL, 6 mmol). The reaction mixture was stirred overnight at room temperature. The reaction was quenched with 20 mL of water and the mixture was extracted with dichloromethane (50 mL×3). The combined organic extracts were washed with 50 mL of 10% citric acid solution and 50 mL of saturated brine successively, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 2-(piperidine-1-carbonyl)-hexahydro-cyclopenta[c]pyrrol-5-one 4a (0.41 g, yield 87%) as a colorless oil.
Workup
- stirringThe reaction mixture was stirred overnight at room temperature
- customThe reaction was quenched with 20 mL of water
- extractionthe mixture was extracted with dichloromethane (50 mL×3)
- washThe combined organic extracts were washed with 50 mL of 10% citric acid solution and 50 mL of saturated brine successively
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-16f6327276664d3ab2a592fbae11e2af
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415349B2
Reaction notes
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