Reaction #53855

ord-6022171bfbfc41a88f67c0c30a82e5ba

Reaction equation

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

Reactants

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

Reagents

None

Solvents

C1CCOC1
THF
C1CCOC1
THF

Conditions

Temperature
-78°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureThe reaction was warmed up to +15° C. for 3.5 h
  2. 2
    OtherThe cooling bath was removed
  3. 3
    workup.ADDITIONTHF was added
  4. 4
    Filtrationfiltered
  5. 5
    OtherAfter evaporation
  6. 6
    workup.DISSOLUTIONthe residue was dissolved in CH2Cl2
  7. 7
    Dryingdried over Na2SO4
  8. 8
    Otherevaporated

Procedure

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

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