Reacción #81467

ord-ec36e245e4bc42cbbd4e9cfcb89b3272

Ecuación de reacción

CCB(CC)c1cccnc1
Diethyl(3-pyridyl)borane
C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(I)=CC[C@@H]12
17-iodo-androsta-5,16-dien-3β-ol
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
→
C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(c3cccnc3)=CC[C@@H]12
17-(3-Pyridyl)androsta-5,16-dien-3β-ol

Reactantes

CCB(CC)c1cccnc1
Diethyl(3-pyridyl)borane
C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(I)=CC[C@@H]12
17-iodo-androsta-5,16-dien-3β-ol
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate

Reactivos

[Cl][Pd][Cl].c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1
bis(triphenylphosphine)palladium (II) chloride

Disolventes

C1CCOC1
THF

Condiciones de reacción

Temperatura
80°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturathe mixture heated
  2. 2
    Temperaturato cool

Procedimiento

Diethyl(3-pyridyl)borane (3.23 g, 22 mmol) from Aldrich Chemical Co. Ltd. was added to a stirred solution of 17-iodo-androsta-5,16-dien-3β-ol (7.96 g, 20 mmol) in THF (120 ml) containing bis(triphenylphosphine)palladium (II) chloride (140 mg, 0.2 mmol). An aqueous solution of sodium carbonate (2M, 50 ml) was then added and the mixture heated, with stirring, by an oil bath at 80° C. for 48 h, and allowed to cool.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05618807uspto-grants-1997_04