Sodium Chloride → 1-Azidomethyl-4-methyl-2-oxabicyclo[2.2.2]octan-3-one
Reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].I[CH2:6][C:7]12[CH2:14][CH2:13][C:10]([CH3:15])([CH2:11][CH2:12]1)[C:9](=[O:16])[O:8]2.[Cl-].[Na+]>CN(C=O)C>[N:1]([CH2:6][C:7]12[CH2:14][CH2:13][C:10]([CH3:15])([CH2:11][CH2:12]1)[C:9](=[O:16])[O:8]2)=[N+:2]=[N-:3]Participants
Conditions
- Temperature
- 100 °C
Procedure
2.6 g of sodium azide was added to a solution of 1.1 g of 1-iodomethyl-4-methyl-2-oxabicyclo[2.2.2]-octan-3-one (Example 28) in 10 ml of DMF. The solution was reacted for 15 hours, while being heated to 100° C. After reaction, 50 ml of an aqueous sodium chloride solution was added to the reaction solution. The solution was then extracted three times with 30 ml of ethyl acetate. The organic layer obtained was washed twice with an aqueous sodium chloride solution and dried over magnesium sulfate. Thereafter, the solvent was removed in vacuo. The oily substance formed was subjected to column chromatography using 5 g of silica gel. From the fraction eluted with hexane and ethyl acetate=1:1, the solvent was removed in vacuo, yielding 0.6 g of 1-azidomethyl-4-methyl-2-oxabicyclo[2.2.2]octan-3-one as a pale yellow oil, which had the following physiochemical properties:
Workup
- customThe solution was reacted for 15 hours
- additionwas added to the reaction solution
- extractionThe solution was then extracted three times with 30 ml of ethyl acetate
- customThe organic layer obtained
- washwas washed twice with an aqueous sodium chloride solution
- dry with materialdried over magnesium sulfate
- customThereafter, the solvent was removed in vacuo
- customThe oily substance formed
- washFrom the fraction eluted with hexane and ethyl acetate=1:1
- customthe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-af5114cd76bb4137a6c3a862f1a14f23
- Source dataset
- uspto-grants-1994_09
- Patent number
- US05344845
Reaction notes
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