반응 #53855

반응 방정식

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

LAH

KHSO4

→

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

용매

THF

THF

반응 조건

후처리

1. 1
   온도The reaction was warmed up to +15° C. for 3.5 h
2. 2
   기타The cooling bath was removed
3. 3
   workup.ADDITIONTHF was added
4. 4
   여과filtered
5. 5
   기타After evaporation
6. 6
   workup.DISSOLUTIONthe residue was dissolved in CH2Cl2
7. 7
   건조dried over Na2SO4
8. 8
   기타evaporated

실험 절차

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).

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