Reacción #640542

Ecuación de reacción

lithium aluminum hydride

ethyl 6-(tert-butyloxycarbonylamino)nicotinate

magnesium sulfate

sodium hydroxide

→

desired product

Rendimiento 89.2%

6-(tert-Butyloxycarbonylamino)-3-pyridylmethanol

Rendimiento 89.2%

Disolventes

diethyl ether

tetrahydrofuran

tetrahydrofuran

water

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Temperaturacooled to 0° C.
3. 3
   workup.STIRRINGstirring
4. 4
   workup.WAITcontinued for 30 minutes
5. 5
   Otrothe solids removed via filtration
6. 6
   Concentraciónthe filtrate concentrated under reduced pressure

Procedimiento

To 4.6 mL (4.6 mmol) of a 1M solution of lithium aluminum hydride in diethyl ether at −40° C. under a nitrogen atmosphere, was added a slution of 618 mg (2.3 mmol) of ethyl 6-(tert-butyloxycarbonylamino)nicotinate from part B in 40 mL of anhydrous tetrahydrofuran. After the addition, this was warmed to room temperature, stirred for 3 hours, cooled to 0° C., and 145 μL of water, 145 μL of 20% sodium hydroxide solution and 290 μL of water were successively added. To the resulting mixture was added 50 mL of tetrahydrofuran and stirring continued for 30 minutes. Anhydrous magnesium sulfate was added, the solids removed via filtration and the filtrate concentrated under reduced pressure to afford 460 mg of the desired product, m/e=224(M+), which was used directly in the next step.

Fuente