Reacción #2195517

ord-fdb8bccf0ba7410f8da57c7675a57199

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@H]3CCC23OCCO3)C1
Ketal
CC(=O)O[C@H]1C=C[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CCC23OCCO3)C1
3β-acetoxy-17,17-ethylenedioxyandrosta-1,5-diene
Cc1ccc(S(=O)(=O)O)cc1.O
toluene-p-sulfonic acid monohydrate
→
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
Rendimiento 98.0%
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
Rendimiento 98.0%

Reactantes

CC(=O)O[C@H]1C=C[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CCC23OCCO3)C1
Ketal
CC(=O)O[C@H]1C=C[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CCC23OCCO3)C1
3β-acetoxy-17,17-ethylenedioxyandrosta-1,5-diene
Cc1ccc(S(=O)(=O)O)cc1.O
toluene-p-sulfonic acid monohydrate

Reactivos

Ninguno

Disolventes

CC(C)=O.O
acetone water

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Concentraciónwas concentrated to half of its volume
  2. 2
    workup.ADDITIONdiluted with a cold half saturated sodium bicarbonate solution
  3. 3
    TemperaturaThe solution was cooled
  4. 4
    Filtraciónfiltered

Procedimiento

Ketal 5 (0.44 g) from Example 1 was dissolved in acetone-water (30 ml, 8:2), and treated with toluene-p-sulfonic acid monohydrate (0.1 g). After the mixture had been stirred at room temperature for 16 hr it was concentrated to half of its volume and diluted with a cold half saturated sodium bicarbonate solution. The solution was cooled, filtered to give white solid compound (0.38 g, 98%), which was further crystallized from methanol. M.p. 185-87° C., purity 99% (LC-MS).

Fuente

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