Reacción #53855

Ecuación de reacción

trans-[4-(Methoxy-methyl-carbamoyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester

LAH

KHSO4

→

trans-(4-Formyl-cyclohexyl)-methyl-carbamic acid tert-butyl ester

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction was warmed up to +15° C. for 3.5 h
2. 2
   OtroThe cooling bath was removed
3. 3
   workup.ADDITIONTHF was added
4. 4
   Filtraciónfiltered
5. 5
   OtroAfter evaporation
6. 6
   workup.DISSOLUTIONthe residue was dissolved in CH2Cl2
7. 7
   Secadodried over Na2SO4
8. 8
   Otroevaporated

Procedimiento

A solution of 2.09 g (55 mmol) LAH in 250 ml THF was cooled (−50° C.) and treated during 25 min with a solution of 15.02 g (50 mmol) of trans-[4-(Methoxy-methyl-carbamoyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester in 250 ml THF. The reaction was warmed up to +15° C. for 3.5 h, cooled (−78° C.) and hydrolyzed with a suspension of 15 g MgSO4.7H2O, 15 g silicagel in 50 ml aqueous 10% KHSO4. The cooling bath was removed, THF was added, the mixture was stirred for 30 min and filtered. After evaporation, the residue was dissolved in CH2Cl2, dried over Na2SO4 and evaporated to yield 12.83 (quantitative) trans-(4-Formyl-cyclohexyl)-methyl-carbamic acid tert-butyl ester, MS: 241 (M).

Fuente