Реакция #657277

Уравнение реакции

methyl iodide

4-benzyloxy-8-methoxy-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-2-one

lithium bis(trimethylsilyl)amide

→

4-benzyloxy-8-methoxy-1-methyl-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-2-one

Растворители

tetrahydrofuran

tetrahydrofuran

Условия реакции

Обработка

1. 1
   workup.STIRRINGStirring
2. 2
   workup.WAITwas continued at room temperature overnight
3. 3
   Другоеthe reaction mixture was quenched with cold saturated aqueous ammonium chloride
4. 4
   ДругоеThe layers were separated
5. 5
   Экстракцияthe aqueous phase extracted twice with ethyl acetate
6. 6
   Промывкаthe combined organic phases washed with brine
7. 7
   Сушкаdried over sodium sulfate
8. 8
   Концентрированиеconcentrated
9. 9
   workup.STIRRINGstirred for 30 minutes
10. 10
    Фильтрацияfiltered
11. 11
    Другоеdried

Методика

To a solution of 4-benzyloxy-8-methoxy-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-2-one (40.0 g, 98.4 mmol) in tetrahydrofuran (500 ml) at 0° C. was added a 1.0 M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (108.3 ml, 108.3 mmol) dropwise over one hour. The mixture was stirred at 0° C. for 30 minutes and at room temperature for 30 minutes, then treated with methyl iodide (6.75 ml, 15.4 g, 108.2 mmol) dropwise at 0° C. over 10 minutes. Stirring was continued at room temperature overnight and the reaction mixture was quenched with cold saturated aqueous ammonium chloride. The layers were separated, the aqueous phase extracted twice with ethyl acetate, the combined organic phases washed with brine, dried over sodium sulfate and concentrated. The residue was suspended in diethyl ether, stirred for 30 minutes, filtered and dried. Yield: 28.6 g of 4-benzyloxy-8-methoxy-1-methyl-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-2-one (compound P3.5) as a solid, mp 139-141° C.

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