Reacción #219164

Ecuación de reacción

p-tolyl-carbamic acid tert-butyl ester

t-BuLi

pentan

cyclopropanecarboxylic acid methoxy-methyl-amide

→

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

Rendimiento 95.1%

Disolventes

Et2O

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato warm to room temperature
2. 2
   workup.STIRRINGstirred for further 1 h before it
3. 3
   Otrowas quenched with aqueous NH4Cl
4. 4
   OtroThe organic phase was isolated
5. 5
   Extracciónthe aqueous phase was extracted with CH2Cl2
6. 6
   Otrothe combined organic phases were dried
7. 7
   Concentraciónconcentrated 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
    OtroThe reaction mixture was evaporated in vacuo
11. 11
    workup.ADDITIONadded aqueous NaHCO3 to pH 7
12. 12
    Extracciónextracted with CH2Cl2
13. 13
    OtroThe combined organic phases were dried
14. 14
    Concentraciónconcentrated in vacuo

Procedimiento

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.

Fuente