Perchloric Acid → HCID 11249146, Verbindung

HRID 1199313Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1199313
C(O[C@H]1CC[C@@]2(C)[C@@H](CC=C3[C@@H]2CC[C@@]2(C)C3=CC[C@@H]2[C@H](C)CCCC(C)C)C1)(=O)C1C=CC=CC=1.[C:37]([O:45][C@H:46]1[CH2:70][CH2:69][C@@:68]2([CH3:71])[C@@H:48]([CH2:49][CH:50]=[C:51]3[C@@H:67]2[CH2:66][CH2:65][C@@:64]2([CH3:72])[C@@:52]43[O:73][C@H:53]4[CH2:54][C@@H:55]2[C@H:56]([CH3:63])[CH2:57][CH2:58][CH2:59][CH:60]([CH3:62])[CH3:61])[CH2:47]1)(=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.Cl(O)(=O)(=O)=O>CC(C)=O>[C:37]([O:45][C@H:46]1[CH2:70][CH2:69][C@@:68]2([CH3:71])[C@@H:48]([CH2:49][CH2:50][C:51]3[C@@H:67]2[CH2:66][CH2:65][C@@:64]2([CH3:72])[C:52]=3[C:53](=[O:73])[CH2:54][C@@H:55]2[C@H:56]([CH3:63])[CH2:57][CH2:58][CH2:59][CH:60]([CH3:62])[CH3:61])[CH2:47]1)(=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Komponenten

5

Edukt 3

HCID 24247Perchloric AcidHCID 14035699HCID 14035699, VerbindungHCID 14696446HCID 14696446, Verbindung2×

Produkt 1

HCID 11249146HCID 11249146, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

In accordance with Scheme III, the epoxidation of (3β,5α)cholesta-7,14-dien-3-ol benzoate (2) to (3β,5α, 15α)-14,15-epoxycholest-7-en-3-ol benzoate (3) is carried out as described in Scheme II. Also when the epoxyolefin (3) is treated with a catalytic amount of a protic acid (preferably 70% perchloric acid) in acetone at a controlled temperature of about 23°-26° C. for 3 hours, the precursor compound (3β,5α)-3-(benzoyloxy)cholest-8(14)en-15-one (6) is obtained. However, it has been discovered that when the preceding reaction is conducted at a temperature of from about 15°-22° C. for 3 hours, the novel intermediate compound (3β,5α)-3-(benzoyloxy)cholest-7-en-15-one (5) is produced Further treatment of (5) with a protic acid (preferably 70% perchloric acid) in acetone at about 23°-26° C. for 2 hours also gives the precursor compound (6) which is refluxed with potassium carbonate in a protic solvent, preferably methanol, as described hereinbefore in Scheme II to give the product (7). The alternate debenzoylation procedures described in Scheme II may also be used to give the product (7).

Quellen und Nachweise

ORD-Eintrag
ord-c30f914b5b2b479984b5c71b99b89b03
Quelldatensatz
uspto-grants-1990_02
Patentnummer
US04900477

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