Реакция #647213

Уравнение реакции

p-tolyl-carbamic acid tert-butyl ester

t-BuLi

pentan

cyclopropanecarboxylic acid methoxy-methyl-amide

→

(2-amino-5-methyl-phenyl)-cyclopropyl-methanone

Выход 95.1%

Растворители

Et2O

Условия реакции

Обработка

1. 1
   Температураto warm to room temperature
2. 2
   workup.STIRRINGstirred for further 1 h before it
3. 3
   Другоеwas quenched with aqueous NH4Cl
4. 4
   ДругоеThe organic phase was isolated
5. 5
   Экстракцияthe aqueous phase was extracted with CH2Cl2
6. 6
   Другоеthe combined organic phases were dried
7. 7
   Концентрированиеconcentrated in vacuo
8. 8
   workup.DISSOLUTIONThe crude material was dissolved CH2Cl2 (15 mL) and TFA (15 mL)
9. 9
   workup.STIRRINGstirred at room temperature for 3 h
10. 10
    ДругоеThe reaction mixture was evaporated in vacuo
11. 11
    workup.ADDITIONadded aqueous NaHCO3 to pH 7
12. 12
    Экстракцияextracted with CH2Cl2
13. 13
    ДругоеThe combined organic phases were dried
14. 14
    Концентрированиеconcentrated in vacuo

Методика

To a stirred solution of p-tolyl-carbamic acid tert-butyl ester (1.0 g, 4.8 mmol) in Et2O (10 mL) under a nitrogen atmosphere was added dropwise a 1.7 M solution of t-BuLi in pentan (6.5 mL, 11.1 mmol) over a 10-min period at −20° C. The mixture was stirred at −10° C. for 2.5 h and then cyclopropanecarboxylic acid methoxy-methyl-amide (0.92 g, 6.3 mmol) was added over 5 min. The mixture was allowed to warm to room temperature and stirred for further 1 h before it was quenched with aqueous NH4Cl. The organic phase was isolated and the aqueous phase was extracted with CH2Cl2, and the combined organic phases were dried and concentrated in vacuo. The crude material was dissolved CH2Cl2 (15 mL) and TFA (15 mL) and stirred at room temperature for 3 h. The reaction mixture was evaporated in vacuo, and added aqueous NaHCO3 to pH 7 and extracted with CH2Cl2. The combined organic phases were dried and concentrated in vacuo to give 0.80 g crude (2-amino-5-methyl-phenyl)-cyclopropyl-methanone as a yellow oil.

Источник