Reacción #162207

Ecuación de reacción

racemic methyl-3-azido-2-hydroxy-1-methyl-cyclohexane-carboxylate

66c

racemic methyl-3-azido-2-hydroxy-1-methyl-cyclohexanecarboxylate

→

methyl-3-amino-2-hydroxy-1-methyl-cyclohexanecarboxylate

Disolventes

MeOH

AcOH

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe mixture was filtered through a celite bed
2. 2
   Lavadowashed with MeOH
3. 3
   OtroThe combined filtrates were evaporated

Procedimiento

A solution of racemic methyl-3-azido-2-hydroxy-1-methyl-cyclohexane-carboxylate, 66c, (0.90 g, 4.22 mmol) in a mixture of MeOH (50 mL) and AcOH (10 mL) was stirred under a hydrogen atmosphere (balloon) with the presence of palladium (0.50 g, 0.47 mmol) overnight at room temperature. The mixture was filtered through a celite bed and washed with MeOH. The combined filtrates were evaporated to provide methyl-3-amino-2-hydroxy-1-methyl-cyclohexanecarboxylate as a oil. Et2O was added and the resulted acetic acid salt was stirred for 0.5 hour and was then filtered to give 1.0 g of racemic methyl-3-amino-2-hydroxy-1-methyl-cyclohexanecarboxylate acetic acid salt as a white solid.

Fuente