反应 #657277

反应方程式

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

溶剂

tetrahydrofuran

tetrahydrofuran

反应条件

后处理

1. 1
   workup.STIRRINGStirring
2. 2
   workup.WAITwas continued at room temperature overnight
3. 3
   其他the reaction mixture was quenched with cold saturated aqueous ammonium chloride
4. 4
   其他The layers were separated
5. 5
   萃取the aqueous phase extracted twice with ethyl acetate
6. 6
   洗涤the combined organic phases washed with brine
7. 7
   干燥dried over sodium sulfate
8. 8
   浓缩concentrated
9. 9
   workup.STIRRINGstirred for 30 minutes
10. 10
    过滤filtered
11. 11
    其他dried

实验过程

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.

来源