Reacción #81464

Ecuación de reacción

17-(3-Pyridyl)-5α-androst-16-en-3α-ol

aluminium isopropoxide

→

title compound

Rendimiento 86.0%

17-(3-Pyridyl)-5α-androst-16-en-3-one

Rendimiento 86.0%

Disolventes

toluene

cyclohexanone

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture heated
2. 2
   Temperaturaunder reflux for 90 min.
3. 3
   Temperaturato cool
4. 4
   Lavadowashed with aqueous trisodium citrate (15% w/v; 2×30 ml)
5. 5
   Secadodried (Na2CO3)
6. 6
   Concentraciónconcentrated
7. 7
   LavadoChromatography, on elution with toluene-methanol (40:1)

Procedimiento

From a solution of 17-(3-Pyridyl)-5α-androst-16-en-3α-ol (1.05g, 3.0 mmol) in dry toluene (60 ml) and cyclohexanone (10 ml) was distilled off part of the solvent (20 ml) to eliminate moisture. After allowing to cool to 90° C., aluminium isopropoxide (1.02 g, 5.0 mmol) was added and the mixture heated under reflux for 90 min. then allowed to cool. The mixture was diluted with diethyl ether (250 ml), washed with aqueous trisodium citrate (15% w/v; 2×30 ml), dried (Na2CO3), and concentrated. Chromatography, on elution with toluene-methanol (40:1), afforded the title compound (0.90 g, 86%) which crystallised from toluene, m.p. 190°-192° C. IR νmax 1713 cm- ; 1H-NMR (CDCl3) inter alia δ 1.04 (3H,s,19-CH3), 1.07 (3H,s, 18-CH3), 5.98 (1M,16-H), 7.22 (1H,m,Py 5-H), 7.64 (1H,m,Py 4-H), 8.46 (1 H,m,Py 6-H), 8.61 (1H,m,Py 2-H); MS m/z 349 (M+). Anal. Calcd: C,82.47; H,8.94; N,4.01. Found: C.82.00; H,8.94; N,3.84%

Fuente