Sodium Carbonate → 3alpha-Acetoxy-17-(3-pyridyl)-5alpha-androst-16-ene

HRID 1451367

Reaktionsgleichung

Reaktionsgleichung von HRID 1451367
C(B(CC)[C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)C.FC(F)(F)S(O[C:18]1[C@:19]2([CH2:36][CH2:35][C@H:34]3[C@@H:24]([CH2:25][CH2:26][C@@H:27]4[C@:32]3([CH3:33])[CH2:31][CH2:30][C@@H:29]([O:37][C:38](=[O:40])[CH3:39])[CH2:28]4)[C@@H:21]2[CH2:22][CH:23]=1)[CH3:20])(=O)=O.C(O[C@@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CCC2=O)C1)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[C:38]([O:37][C@@H:29]1[CH2:30][CH2:31][C@@:32]2([CH3:33])[C@@H:27]([CH2:26][CH2:25][C@@H:24]3[C@@H:34]2[CH2:35][CH2:36][C@@:19]2([CH3:20])[C@H:21]3[CH2:22][CH:23]=[C:18]2[C:4]2[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=2)[CH2:28]1)(=[O:40])[CH3:39]

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 101996Androsterone acetateHCID 6428513-(Diethylboryl)pyridineHCID 10095984HCID 10095984, Verbindung

Produkt 1

HCID 99779013alpha-Acetoxy-17-(3-pyridyl)-5alpha-androst-16-eneAusbeute 82,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The method followed that described in Example 1, using in step (b) diethyl(3-pyridyl)borane (1.41 g, 9.6 mmol), 3α-acetoxy-5α-androst-16-en-17-yl trifluoromethanesulphonate (3.44 g, 7.4 mmol), prepared from the 3α-acetoxy-5α-androstan-17-one by the method of step (a), THF (40 ml), bis(triphenylphosphine)palladium(II) chloride (52 mg, 0.07 mmol), and aqueous sodium carbonate (2M, 15 mmol). Chromatography, on elution with light petroleum-diethyl ether (2:1), afforded the title compound (2.39 g, 82%), 1H-NMR (CDCl3) inter alia δ0.85(3H,s, 19-CH3), 1.01(3H,s,18-CH3), 2.06(3H,s,CH3CO2), 5.02(1H,m,3β-H), 6.00(1H,m,16-H), 7.24(1H,m,Py 5-H), 7.68(1H,m,Py 4-H), 8.47(1H,m,Py 6-H), 8.63(1H,m,Py 2-H); MS m/z 393 (M+).

Aufarbeitung

  1. washChromatography, on elution with light petroleum-diethyl ether (2:1)

Quellen und Nachweise

ORD-Eintrag
ord-e95ccfd48be04217a2f0601600591b1f
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05604213

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