Diethyl Ether → 17beta,19-Di-(1-methoxy-1-cyclopentyloxy)-androst-4-en-3beta-ol

HRID 371809

Reaktionsgleichung

Reaktionsgleichung von HRID 371809
O[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@]1(CO)C(=CC(=O)CC1)CC3.[CH3:23][O:24][C:25]1([O:30][C@H:31]2[CH2:36][CH2:35][C@H:34]3[C@H:37]4[C@H:55]([CH2:56][CH2:57][C@:32]23[CH3:33])[C@:45]2([CH2:46][O:47][C:48]3([O:53][CH3:54])[CH2:52][CH2:51][CH2:50][CH2:49]3)[C:40](=[CH:41][C:42](=[O:58])[CH2:43][CH2:44]2)[CH2:39][CH2:38]4)[CH2:29][CH2:28][CH2:27][CH2:26]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC>O1CCCC1>[CH3:23][O:24][C:25]1([O:30][C@H:31]2[CH2:36][CH2:35][C@H:34]3[C@H:37]4[C@H:55]([CH2:56][CH2:57][C@:32]23[CH3:33])[C@:45]2([CH2:46][O:47][C:48]3([O:53][CH3:54])[CH2:52][CH2:51][CH2:50][CH2:49]3)[C:40](=[CH:41][C@@H:42]([OH:58])[CH2:43][CH2:44]2)[CH2:39][CH2:38]4)[CH2:26][CH2:27][CH2:28][CH2:29]1

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 15096819-HydroxytestosteroneHCID 21226445Aluminium lithium hydrideHCID 8673567817beta,19-Di-(1-methoxy-1-cyclopentyloxy)-androst-4-en-3-one

Produkt 1

HCID 8673567717beta,19-Di-(1-methoxy-1-cyclopentyloxy)-androst-4-en-3beta-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The compound 17β,19-dihydroxyandrost-4-en-3-one is similarly etherified to form the 17β-OR4, 19-OR1, derivatives of androst-4-en-3-one. Reduction as previously described yields the corresponding 3-hydroxy analogues. For example, 17β,19-dihydroxyandrost-4-en-3-one is converted to 17β,19-di-triphenylsiloxyandrost-4-en-3-one and 17β,19-di-(1-methoxy-1-cyclopentyloxy)-androst-4-en-3-one as previously described. These compounds are then reduced using lithium aluminum hydride in an ether or tetrahydrofuran solution to produce 17β,19-di-triphenylsiloxyandrost-4-en-3β-ol and 17β,19-di-(1-methoxy-1-cyclopentyloxy)-androst-4-en-3β-ol, respectively.

Quellen und Nachweise

ORD-Eintrag
ord-c843252dc8e045bd9c6a786e7333510e
Quelldatensatz
uspto-grants-1978_05
Patentnummer
US04087524

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