Reacción #52194

Ecuación de reacción

40

4-Formylphenyloxycarbonyl-glutamic acid di-tert-butyl ester

methylamine THF

→

amine

Rendimiento 78.0%

4-(Methyaminomethyl)phenyloxycarbonyl-glutamic acid di-tert-butyl ester

Rendimiento 78.0%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter removal of solvents
2. 2
   workup.DISSOLUTIONthe residual oil was dissolved in methanol (80 mL)
3. 3
   Otroplaced in an ice-bath
4. 4
   workup.ADDITIONTo the above solution was added sodium borohydride in small portions over 30 min
5. 5
   Otrosolvent was then evaporated
6. 6
   OtroAfter separation
7. 7
   Secadothe organic phase was dried over anhydrous MgSO4
8. 8
   Otrorotary evaporated
9. 9
   Otrodried in vacuum

Procedimiento

A stirred solution of 40 (6.1 g, 14.9 mmol) in dichloromethane (50 mL) was treated with 2 N methylamine-THF solution (10 mL) at 0° C. overnight. After removal of solvents, the residual oil was dissolved in methanol (80 mL) and placed in an ice-bath. To the above solution was added sodium borohydride in small portions over 30 min. The reaction solution was kept at 0° C. for 1 hour, and solvent was then evaporated. The residue was worked up with brine and dichloromethane. After separation, the organic phase was dried over anhydrous MgSO4, rotary evaporated and dried in vacuum. The crude amine 41 (5.4 g, 78%) was obtained as a light yellow glassy solid.

Fuente