Sodium Hydroxide → (3alpha,5alpha)-17-(3-Pyridinyl)androst-16-en-3-ol

HRID 1451368

Reaktionsgleichung

C([O:4][C@@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH:13]=[C:14]2[C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[CH2:6]1)(=O)C.[OH-].[Na+]>CO>[N:26]1[CH:27]=[CH:28][CH:29]=[C:24]([C:14]2[C@:15]3([CH2:17][CH2:18][C@H:19]4[C@@H:10]([CH2:9][CH2:8][C@@H:7]5[C@:20]4([CH3:23])[CH2:21][CH2:22][C@@H:5]([OH:4])[CH2:6]5)[C@@H:11]3[CH2:12][CH:13]=2)[CH3:16])[CH:25]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

The method followed that described in Example 2, but using 3α-acetoxy-17-(3 -pyridyl)-5α-androst-16-ene (2.33 g, 5.9 mmol), methanol (40 ml), aqueous sodium hydroxide (10% w/v, 8 ml), and the mixture was heated at 80° C. for 20 min. Chromatography, on elution with toluene-methanol (40:1 ), afforded the title compound (1.62 g, 78%) which crystallised from toluene, m.p. 198°-199° C.; 1H-NMR(CDCl3) inter alia. δ0.84(3H,s,19-CH3), 1.00(3H,s,18-CH3), 4.06(1H,m,3β-H), 5.97(1H,m,16-H), 7.21(1H,m,Py 5-H), 7.64(1H,m,Py 4-H), 8.45(1H,m,Py 6-H), 8.61(1H,m,Py 2-H). Anal. Calcd: C, 82.00; H,9.46; N,3.99. Found: C,81.78; H,9.47; N.3.96%.

Aufarbeitung

washChromatography, on elution with toluene-methanol (40:1 )

Quellen und Nachweise

ORD-Eintrag: ord-d4a43d61448c4ca68f054809f4ee27ff
Quelldatensatz: uspto-grants-1997_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05604213

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