Reaction equation
[H-].[Na+].[CH:3]12[CH2:8][CH:7]1[C:6](=[O:9])[NH:5][C:4]2=[O:10].I[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].CN(C)C=O>O1CCCC1.ClCCl>[CH2:12]([N:5]1[C:6](=[O:9])[CH:7]2[CH:3]([CH2:8]2)[C:4]1=[O:10])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]Participants
Procedure
Sodium hydride (0.11 g) was added to a solution of 3-azabicyclo[3.1.0]hexane-2,4-dione (0.3 g) in dry tetrahydrofuran (10 ml) under a nitrogen atmosphere at room temperature. The suspension was stirred for 5 minutes and 1-iodoheptane (0.61 g) was then added in one portion to the reaction mixture. After stirring for two hours at room temperature, dimethylformamide (5 ml) was added and the reaction mixture was stirred for a further 16 hours at room temperature. The reaction mixture was diluted with dichloromethane and then partitioned with water (20 ml). The aqueous phase was extracted with dichloromethane (20 ml) and the combined organic extracts were washed with water (2×20 ml), dried (MgSO4) and evaporated in vacuo. The residue was purified by chromatography on silica gel (50 g) using 25-30% ethyl acetate/hexane as eluant to give the title compound as a colourless oil.
Workup
- stirringAfter stirring for two hours at room temperature
- stirringthe reaction mixture was stirred for a further 16 hours at room temperature
- custompartitioned with water (20 ml)
- extractionThe aqueous phase was extracted with dichloromethane (20 ml)
- washthe combined organic extracts were washed with water (2×20 ml)
- dry with materialdried (MgSO4)
- customevaporated in vacuo
- customThe residue was purified by chromatography on silica gel (50 g)
Sources & evidence
- ORD record
- ord-d7033219963e47e58c27ef5289b19e91
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06130241
Linked notes
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