Potassium Carbonate → Colestolone

HRID 1199312Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1199312
C([O:9][C@H:10]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C@@H:12]([CH2:13][CH2:14][C:15]3[C@@H:31]2[CH2:30][CH2:29][C@@:28]2([CH3:36])[C:16]=3[C:17](=[O:37])[CH2:18][C@@H:19]2[C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:11]1)(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO>[OH:9][C@H:10]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C@@H:12]([CH2:13][CH2:14][C:15]3[C@@H:31]2[CH2:30][CH2:29][C@@:28]2([CH3:36])[C:16]=3[C:17](=[O:37])[CH2:18][C@@H:19]2[C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:11]1

Komponenten

4

Edukt 2

HCID 11430Potassium CarbonateHCID 11249146HCID 11249146, Verbindung

Produkt 1

HCID 10046567Colestolone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Compound (4) does not show the characteristic streaking of the epoxide (3) by thin layer chromatography, using 10% ethyl acetate/hexane as the solvent system, on silica gel plates, but rather provides a discrete band at an Rf of about 0.1-0.2. The compound treated with a protic acid (preferably 70% perchloric acid) for 2 hours to obtain the precursor (3β,5α)-3-(benzoyloxy)cholest-8(14)en-15-one (6). The precursor (6) is dissolved in a protic solvent, preferably methanol, and treated with potassium carbonate as hereinbefore described to provide the desired product (7). The alternate procedures of Scheme II for the debenzoylation may also be used.

Quellen und Nachweise

ORD-Eintrag
ord-dbac642e3e36401dad3b4d995c8a12db
Quelldatensatz
uspto-grants-1990_02
Patentnummer
US04900477

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