Dimethyl Sulfoxide → 6,7-dihydro-5H-spiro[imidazo[1,5-a]pyridine-8,2'-oxirane]
Reaction equation
[H-].[Na+].CS(C)=O.[I-].[CH3:8][S+](C)C.[CH:12]1[N:13]=[CH:14][N:15]2[CH2:20][CH2:19][CH2:18][C:17](=[O:21])[C:16]=12>CCCCC.O1CCCC1.CN(C)C=O.[Cl-].[Na+].O>[O:21]1[CH2:8][C:17]21[CH2:18][CH2:19][CH2:20][N:15]1[CH:14]=[N:13][CH:12]=[C:16]21Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 60 °C
Procedure
Sodium hydride (22 mmol) washed with pentane is admixed under argon with 20 ml of dimethyl sulphoxide. The mixture is heated at 60° C. for an hour and then diluted with 5 ml of tetrahydrofuran. The mixture is cooled to 0° C. and a solution of 21 mmol of trimethyl-sulphonium iodide in 5 ml of N,N-dimethylformamide is added at 0° C., after which the mixture is stirred for 10 minutes. A solution of 20 mmol of 6,7-dihydro-5H-imidazo[1,5-a]pyridin-8-one [426219-51-4] in 5 ml of N,N-dimethylformamide is added and the reaction mixture is stirred at 60° C. for 18 hours. The reaction mixture is poured into cold brine and extracted with tert-butyl methyl ether. The combined organic phases are washed with brine, dried with sodium sulphate and evaporated. From the residue the title compound is identified by means of flash chromatography (SiO2 60 F) on the basis of the Rf value.
Workup
- temperatureThe mixture is cooled to 0° C.
- stirringthe reaction mixture is stirred at 60° C. for 18 hours
- extractionextracted with tert-butyl methyl ether
- washThe combined organic phases are washed with brine
- dry with materialdried with sodium sulphate
- customevaporated
Sources & evidence
- ORD record
- ord-c8da428b86274a3eba72701e2eee38aa
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08071773B2
Reaction notes
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