Réaction #53855

Équation de réaction

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

LAH

KHSO4

→

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

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction was warmed up to +15° C. for 3.5 h
2. 2
   AutreThe cooling bath was removed
3. 3
   workup.ADDITIONTHF was added
4. 4
   Filtrationfiltered
5. 5
   AutreAfter evaporation
6. 6
   workup.DISSOLUTIONthe residue was dissolved in CH2Cl2
7. 7
   Séchagedried over Na2SO4
8. 8
   Autreevaporated

Mode opératoire

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).

Source