Isopropyl iodide → HCID 23459827, compound
Reaction equation
[CH:1](NC(C)C)([CH3:3])[CH3:2].C([Li])CCC.[O:13]=[C:14]1[N:21]2[C:16]([CH3:24])([CH2:17][CH2:18][O:19][C:20]2([CH3:23])[CH3:22])[CH2:15]1.C(I)(C)C>CCOC(C)=O.CN(C)P(N(C)C)(N(C)C)=O.C1COCC1>[O:13]=[C:14]1[N:21]2[C:16]([CH3:24])([CH2:17][CH2:18][O:19][C:20]2([CH3:23])[CH3:22])[CH:15]1[CH:1]([CH3:3])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- -78 °C
Procedure
THF, 20 ml is placed under N2, treated with 1.54 ml diisopropylamine and cooled to -78° C. A solution of n-butyl lithium (1.97 M in hexane; 5.6 ml) is added dropwise over 5 min. The reaction mixture is stirred at -78° C. for 10 min. and then treated with 8-oxo-2,2,6-trimethyl-3-oxa-1-azabicyclo[4.2.0]octane (0.0079 mmole) ml THF added dropwise over 5 min. After another 10 min. hexamethylphosphoramide 1.97 ml is added. The mixture is stirred another 10 min., then treated with 2 ml of isopropyl iodide. The reaction mixture is stirred at -78° C. for 15 min. and allowed to warm to 25° C. and stirred for 15 min. The reaction mixture is diluted with EtOAc, washed once with pH 7 phosphate buffer then dried and evaporated. The residue is chromatographed on silica gel using 25% EtOAc/C6H6 as eluant to give 8-oxo-2,2,6-trimethyl-7-isopropyl-3-oxa-1-azabicyclo[4.2.0]-octane.
Workup
- additionadded dropwise over 5 min
- stirringThe mixture is stirred another 10 min.
- stirringThe reaction mixture is stirred at -78° C. for 15 min.
- temperatureto warm to 25° C.
- stirringstirred for 15 min
- washwashed once with pH 7 phosphate buffer
- customthen dried
- customevaporated
- customThe residue is chromatographed on silica gel using 25% EtOAc/C6H6 as eluant
Sources & evidence
- ORD record
- ord-9bd8da545a5d49f2a7cee48cfdc8813d
- Source dataset
- uspto-grants-1981_05
- Patent number
- US04269873
Reaction notes
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