Water → (2beta,3alpha,17beta)-17-Methoxv-2-(piperazin-1-yl)androstan-3-ol

HRID 244255Notizen

Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

To compound 35 (100 mg, 0.33 mmol) was added water (1 mL) and piperazine (3.5g, 41 mmol). The solution was subsequently heated at 150° C. over a period of 24 h. The resulting mixture was diluted with dichloromethane (50 mL) and washed with water, dried with Na2SO4, filtered and evaporated under reduced pressure. The crude compound was purified by flash chromatography (DCM/MeOH: 9:1 containing 0.5% of TEA) to yield compound 36 (90 mg, 70%). 1H NMR (CDCl3) δ: 0.72 (s, 18-CH3), 0.82 (s, 19-CH3), 0.65-2.05 (residual CH and CH2), 2.38, 2.60 and 2.86 (3m, 4×CH2N and 2α-CH), 3.18 (t, J=8.2 Hz, 17α-CH), 3.31 (s, OCH3), 3.82 (m, 3β-CH).

Aufarbeitung

washwashed with water
dry with materialdried with Na2SO4
filtrationfiltered
customevaporated under reduced pressure
customThe crude compound was purified by flash chromatography (DCM/MeOH: 9:1 containing 0.5% of TEA)

Quellen und Nachweise

ORD-Eintrag: ord-c2526a81e14946bf9f0ee570062773cf
Quelldatensatz: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08653054B2

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