Reaktion #53855

ord-6022171bfbfc41a88f67c0c30a82e5ba

Reaktionsgleichung

CON(C)C(=O)[C@H]1CC[C@H](N(C)C(=O)OC(C)(C)C)CC1
trans-[4-(Methoxy-methyl-carbamoyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester
[Al+3].[H-].[H-].[H-].[H-].[Li+]
LAH
O=S(=O)([O-])O.[K+]
KHSO4
→
CN(C(=O)OC(C)(C)C)[C@H]1CC[C@H](C=O)CC1
trans-(4-Formyl-cyclohexyl)-methyl-carbamic acid tert-butyl ester

Edukte

CON(C)C(=O)[C@H]1CC[C@H](N(C)C(=O)OC(C)(C)C)CC1
trans-[4-(Methoxy-methyl-carbamoyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester
[Al+3].[H-].[H-].[H-].[H-].[Li+]
LAH
—
MgSO4.7H2O
O=S(=O)([O-])O.[K+]
KHSO4

Reagenzien

Keine

Lösungsmittel

C1CCOC1
THF
C1CCOC1
THF

Reaktionsbedingungen

Temperatur
-78°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturThe reaction was warmed up to +15° C. for 3.5 h
  2. 2
    SonstigeThe cooling bath was removed
  3. 3
    workup.ADDITIONTHF was added
  4. 4
    Filtrationfiltered
  5. 5
    SonstigeAfter evaporation
  6. 6
    workup.DISSOLUTIONthe residue was dissolved in CH2Cl2
  7. 7
    Trocknendried over Na2SO4
  8. 8
    Sonstigeevaporated

Vorschrift

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).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06858651B2uspto-grants-2005_02