Tetrahydrofuran → 1-Methyl-4-(pyridin-3-yl)azetidin-2-one
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[NH:10][C:9](=[O:11])[CH2:8]2)[CH:2]=1.[H-].[Na+].[Cl-].[NH4+].O1CCC[CH2:17]1>>[CH3:17][N:10]1[CH:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH2:8][C:9]1=[O:11]Participants
Procedure
To a solution of 0.105 g (0.71 mmole) 4-(pyridin-3-yl)azetidin-2-one in 5 ml of dry tetrahydrofuran at stirring under argon atmosphere 0.113 g (2.83 mmole) 60% dispersion of sodium hydride in mineral oil was added. After the sparkling ceased at stirring and ice cooling 0.066 ml (0.150 g, 1.06 mmole) iodomethane was added and stirred for 2 hours. Carefully 10 ml of saturated aqueous ammonium chloride solution was added and stirred for 10 minutes. The reaction mixture was filtered and the aqueous solution was extracted with 5×10 ml of chloroform and the combined solutions were dried over magnesium sulfate and evaporated on rotavapor at 35° C. The residue (0.112 g) was purified by column chromatography on 10 g of silica gel with benzene-diethylamine 8-2 furnishing 0.0674 g (59%) pure product.
Workup
- additionwas added
- stirringstirred for 2 hours
- stirringstirred for 10 minutes
- filtrationThe reaction mixture was filtered
- extractionthe aqueous solution was extracted with 5×10 ml of chloroform
- dry with materialthe combined solutions were dried over magnesium sulfate
- customevaporated on rotavapor at 35° C
- customThe residue (0.112 g) was purified by column chromatography on 10 g of silica gel with benzene-diethylamine 8-2 furnishing 0.0674 g (59%) pure product
Sources & evidence
- ORD record
- ord-0bae63b15589466ba03af76c1c7e7287
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09440948B2
Reaction notes
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