Reacción #2383816

ord-776f414ed8ed44399b6c9cecfe22c533

Ecuación de reacción

C=CCCC1CCCCc2noc(=O)n21
product
C=CCCC1CCCCc2noc(=O)n21
5-(3-butenyl)-6,7,8,9-tetrahydro-3H,5H-[1,2,4]oxadiazolo[4,3-a]azepin-3-one
[Na+].[O-][I+3]([O-])([O-])[O-]
sodium periodate
→
O=CCCC1CCCCc2noc(=O)n21
title compound
O=CCCC1CCCCc2noc(=O)n21
6,7,8,9-tetrahydro-3-oxo-3H,5H-[1,2,4]oxadiazolo[4,3-a]azepine-5-propanal

Reactantes

C=CCCC1CCCCc2noc(=O)n21
product
C=CCCC1CCCCc2noc(=O)n21
5-(3-butenyl)-6,7,8,9-tetrahydro-3H,5H-[1,2,4]oxadiazolo[4,3-a]azepin-3-one
[Na+].[O-][I+3]([O-])([O-])[O-]
sodium periodate

Reactivos

[O]=[Os](=[O])(=[O])=[O]
osmium tetraoxide

Disolventes

O
Water
C1COCCO1
dioxane
O
water

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Extracciónthe solution is extracted with CH2Cl2
  2. 2
    SecadoThe organic layer is dried over magnesium sulfate
  3. 3
    Filtraciónfiltered

Procedimiento

To a solution of the product of Example 18 in dioxane and water is added sodium periodate and osmium tetraoxide. The reaction is stirred at room temperature and monitored by thin layer chromatography. Water is added to the reaction mixture and the solution is extracted with CH2Cl2. The organic layer is dried over magnesium sulfate, filtered, and stripped of all solvent under reduced pressure to afford the title compound.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US06489323B1uspto-grants-2002_12