1beta-Methyl-5alpha-androstane-3beta,17beta,19-triol 3,17-diacetate → 3beta,17beta-Dihydroxy-1beta-methyl-5alpha-androstan-19-one diacetate

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Reaktionsgleichung

CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[C:14]([O:17][C@H:18]1[CH2:35][C@@H:34]([CH3:36])[C@@:33]2([CH2:37][OH:38])[C@@H:20]([CH2:21][CH2:22][C@@H:23]3[C@@H:32]2[CH2:31][CH2:30][C@@:28]2([CH3:29])[C@H:24]3[CH2:25][CH2:26][C@@H:27]2[O:39]C(=O)C)[CH2:19]1)(=[O:16])[CH3:15]>CC(C)=O>[C:14]([OH:17])(=[O:16])[CH3:15].[C:14]([OH:17])(=[O:16])[CH3:15].[OH:17][C@H:18]1[CH2:35][C@@H:34]([CH3:36])[C@@:33]2([CH:37]=[O:38])[C@@H:20]([CH2:21][CH2:22][C@@H:23]3[C@@H:32]2[CH2:31][CH2:30][C@@:28]2([CH3:29])[C@H:24]3[CH2:25][CH2:26][C@@H:27]2[OH:39])[CH2:19]1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

One equivalent of Jones reagent is added dropwise to a stirred solution of 1β-methyl-5α-androstane-3β,17β,19-triol 3,17-diacetate in acetone chilled to 0° C. After 15 minutes at 0° C., the acetone layer is poured onto ice water. The solid which forms is filtered and crystallized from an ether-hexane solution to yield 3β,17β-dihydroxy-1β-methyl-5α-androstan-19-one diacetate. This material is dissolved in aqueous methanol containing sodium carbonate and the solution heated at its reflux temperature for about 4 hours. The cooled solution is poured onto water and filtered. The solid which forms is collected and is crystallized from an ether-hexane solution to yield 3β,17β-dihydroxy-1β-methyl-5α-androstan-19-one.

Aufarbeitung

filtrationThe solid which forms is filtered
customcrystallized from an ether-hexane solution

Quellen und Nachweise

ORD-Eintrag: ord-c3cb3cd5bbb0437ea1b301d138d0eb30
Quelldatensatz: uspto-grants-1978_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04071625

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