Diethyl Ether → 3-Acetoxy-17-(3-pyridyl)androsta-3,5,16-triene

HRID 53188

Reaktionsgleichung

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[C@:8]3([CH2:25][CH2:24][C@H:23]4[C@@H:13]([CH2:14][CH2:15][C:16]5[C@:21]4([CH3:22])[CH2:20][CH2:19][C:18](=[O:26])[CH:17]=5)[C@@H:10]3[CH2:11][CH:12]=2)[CH3:9])[CH:2]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:38]([O:40]CC)[CH3:39]>C(OC(C)=C)(=O)C>[C:38]([O:26][C:18]1[CH2:19][CH2:20][C@@:21]2([CH3:22])[C:16](=[CH:15][CH2:14][C@@H:13]3[C@@H:23]2[CH2:24][CH2:25][C@@:8]2([CH3:9])[C@H:10]3[CH2:11][CH:12]=[C:7]2[C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH:17]=1)(=[O:40])[CH3:39]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

17-(3-pyridyl)androsta-4,16-dien-3-one (174 mg, 0.50 mmol) was dissolved in isopropenyl acetate (2 ml). p-Toluenesulfonic acid (130 mg, 0.68 mmol) was then added and the mixture heated at 80° C. for 12 h. After allowing to cool the mixture was poured into diethyl ether, washed with saturated aqueous sodium bicarbonate, dried (Na2CO3) and concentrated. Chromatography on elution with light petroleum--diethyl ether (1:1), afforded the title compound (86 mg, 44%), IR νmax 1755 cm-1, 1H-NMR (CDCl3) inter alia δ1.05 (6H,s,18-CH3 and 19-CH3), 2.15 (3H,s,COCH3) 5.44 (1 H,m,6-H), 5.72(1H,m,4-H), 6.00 (1H,m,16-H), 7.25 (1H,m,Py 5-H), 7.66 (1H,m,Py 4-H), 8.47 (1H,M,Py 6H), 8.63 (1H,m,Py 2-H). MS m/z 389 (M+).

Aufarbeitung

temperatureto cool the mixture
washwashed with saturated aqueous sodium bicarbonate
dry with materialdried (Na2CO3)
concentrationconcentrated
washChromatography on elution with light petroleum--diethyl ether (1:1)

Quellen und Nachweise

ORD-Eintrag: ord-9aa072fa2ac64f048b84e7bff075a0bb
Quelldatensatz: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05618807

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