تفاعل #53855

معادلة التفاعل

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

LAH

KHSO4

→

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

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction was warmed up to +15° C. for 3.5 h
2. 2
   أخرىThe cooling bath was removed
3. 3
   workup.ADDITIONTHF was added
4. 4
   ترشيحfiltered
5. 5
   أخرىAfter evaporation
6. 6
   workup.DISSOLUTIONthe residue was dissolved in CH2Cl2
7. 7
   تجفيفdried over Na2SO4
8. 8
   أخرىevaporated

الإجراء التجريبي

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).

المصدر