Reacción #219277

ord-daa05a7ddeb148df9d3a671b4d156bfb

Ecuación de reacción

O=C1CCC2(CC1)OCCO2
1,4-Dioxa-spiro[4.5]decan-8-one
CC(C)(C)S(N)=O
2-Methyl-propane-2-sulfinic acid amide
O=C([O-])O.[Na+]
NaHCO3
CC(C)(C)S(=O)N=C1CCC2(CC1)OCCO2
Compound 15
Rendimiento 45.8%
CC(C)(C)S(=O)N=C1CCC2(CC1)OCCO2
2-Methyl-propane-2-sulfinic acid (1,4-dioxa-spiro[4.5]dec-8-ylidene)-amide
Rendimiento 45.8%

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otroby flushing with N2(g) for 30 min
  2. 2
    Filtraciónfollowed by filtration
  3. 3
    Lavadoan EtOAc rinse
  4. 4
    SecadoThe organic layer was dried with MgSO4
  5. 5
    Filtraciónfiltered
  6. 6
    Concentraciónconcentrated under reduced pressure

Procedimiento

An oven dried round-bottom flask was cooled to room temperature by flushing with N2(g) for 30 min. 1,4-Dioxa-spiro[4.5]decan-8-one (1.35 g, 8.66 mmol) (dissolved in 12 mL THF), 2-Methyl-propane-2-sulfinic acid amide (1.0 g, 8.25 mmol) (dissolved in THF), and titanium(IV) ethoxide (3.77 g, 16.50 mmol) were added. The reaction was stirred for 4 h at room temperature. To the mixture was added 15 mL saturated NaHCO3 followed by filtration and an EtOAc rinse. The organic layer was dried with MgSO4, filtered and concentrated under reduced pressure yielding 0.98 g of Compound 15.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07385085B2uspto-grants-2008_06