Reaktion #1475479

ord-b16849974ee747bf8ed9716b1997075f

Reaktionsgleichung

CSCOc1cccc2c1CC(NC(C)=O)C2=O
residue
CSCOc1cccc2c1CC(NC(C)=O)C2=O
2-acetylamino-4-(methylthiomethoxy)-1-indanone
[Al+3].[H-].[H-].[H-].[H-].[Li+]
LiAlH4
O=S(=O)([O-])[O-].[Na+].[Na+]
Na2SO4
→
CCN[C@@H]1Cc2c(OCSC)cccc2[C@H]1O
crude product
CCN[C@@H]1Cc2c(OCSC)cccc2[C@H]1O
trans-2-ethylamino-4-(methylthiomethoxy)-1-indanol

Edukte

CSCOc1cccc2c1CC(NC(C)=O)C2=O
residue
CSCOc1cccc2c1CC(NC(C)=O)C2=O
2-acetylamino-4-(methylthiomethoxy)-1-indanone
[Al+3].[H-].[H-].[H-].[H-].[Li+]
LiAlH4
O=S(=O)([O-])[O-].[Na+].[Na+]
Na2SO4

Reagenzien

Keine

Lösungsmittel

C1CCOC1
THF
C1CCOC1
THF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturThe mixture is refluxed for one hour
  2. 2
    workup.ADDITIONafter completion of the addition
  3. 3
    TemperaturThe mixture is cooled
  4. 4
    Sonstigeto quench the excess LiAlH4
  5. 5
    workup.ADDITIONMethylene chloride and solid anhydrous Na2SO4 is added
  6. 6
    Filtrationthe mixture is filtered
  7. 7
    EinengenConcentration

Vorschrift

The residue from Step D is dissolved in 50 ml of THF and added to 3.8 g (0.1 m) of LiAlH4 in 50 ml of THF dropwise. The mixture is refluxed for one hour after completion of the addition. The mixture is cooled and sufficient saturated aqueous Na2SO4 solution is added to quench the excess LiAlH4. Methylene chloride and solid anhydrous Na2SO4 is added and the mixture is filtered. Concentration provides the crude product.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04431647uspto-grants-1984_02