Reacción #2195518

ord-06f27a32e6cc4bcebcbdf738eab0451e

Ecuación de reacción

CC(=O)O[C@H]1C=C[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]32)C1
compound 6
CC(=O)O[C@H]1C=C[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]32)C1
3β-acetoxyandrosta-1,5-dien-17-one
O=C([O-])[O-].[K+].[K+]
potassium carbonate
→
C[C@]12C=C[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
3β-hydroxyandrosta-1,5-dien-17-one

Reactantes

CC(=O)O[C@H]1C=C[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]32)C1
compound 6
CC(=O)O[C@H]1C=C[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]32)C1
3β-acetoxyandrosta-1,5-dien-17-one
O=C([O-])[O-].[K+].[K+]
potassium carbonate

Reactivos

Ninguno

Disolventes

CO.O
methanol water

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    ConcentraciónSolution was concentrated
  2. 2
    workup.ADDITIONdiluted with cold water
  3. 3
    Temperaturacooled
  4. 4
    Filtraciónthe precipitated solid was filtered
  5. 5
    Otrocrystallized from methanol

Procedimiento

A mixture of compound 6 (0.25 g) and potassium carbonate (0.3 g) in methanol-water (15 ml, 9:1) was stirred at room temperature for 8 hr. Solution was concentrated diluted with cold water, cooled and the precipitated solid was filtered, and crystallized from methanol. White solid, mp. 138-40° C.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07514420B2uspto-grants-2009_04