Allyl bromide → HCID 69651218, compound
Reaction equation
[CH3:1][C:2]1([CH3:18])[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH:5]([C:14]([O:16][CH3:17])=[O:15])[CH2:4][O:3]1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH2:29](Br)[CH:30]=[CH2:31].[Cl-].[NH4+]>C1COCC1.C1(C)C=CC=CC=1>[CH2:31]([C:5]1([C:14]([O:16][CH3:17])=[O:15])[CH2:4][O:3][C:2]([CH3:18])([CH3:1])[N:6]1[C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])[CH:30]=[CH2:29]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
10 g of 3-tert-butyl 4-methyl 2,2-dimethyloxazolidine-3,4-dicarboxylate were dissolved in 270 ml of THF. After cooling to −78° C., 100 ml of a 0.5 M solution of KHMDS in toluene were added dropwise. After stirring at −78° C. for 30 min, 5.4 ml of allyl bromide were added dropwise. The mixture was allowed slowly to reach room temperature and was stirred for 14 h. The reaction was then stopped by adding 400 ml of saturated ammonium chloride solution. The THF was removed in vacuo and the aqueous phase was extracted 3 times with 150 ml of ethyl acetate each time. The combined organic phases were washed once with 300 ml of saturated sodium chloride solution and dried with MgSO4. The solvents were removed in vacuo and the residue was chromatographed on silica gel.
Workup
- customto reach room temperature
- stirringwas stirred for 14 h
- customThe THF was removed in vacuo
- extractionthe aqueous phase was extracted 3 times with 150 ml of ethyl acetate each time
- washThe combined organic phases were washed once with 300 ml of saturated sodium chloride solution
- dry with materialdried with MgSO4
- customThe solvents were removed in vacuo
- customthe residue was chromatographed on silica gel
Sources & evidence
- ORD record
- ord-78a828c1e6ab4e6a84be6e28b2a5ac46
- Source dataset
- uspto-grants-2006_03
- Patent number
- US07008957B2
Reaction notes
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