HCID 131711025, compound → 5alpha-Androstane

HRID 1834957Notes

Reaction equation

HRID 1834957 reaction equation
C(O[C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH2:23]OC(=O)C)[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2OC)[CH2:6]1)(=O)C>CCOCC>[CH3:16][C@:15]12[CH2:17][CH2:18][C@H:19]3[C@@H:10]([CH2:9][CH2:8][C@@H:7]4[C@:20]3([CH3:23])[CH2:21][CH2:22][CH2:5][CH2:6]4)[C@@H:11]1[CH2:12][CH2:13][CH2:14]2

Participants

3

Reactant 1

HCID 131711025HCID 131711025, compound

Product 1

HCID 941445alpha-Androstane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

More particularly, a zinc and acetic acid cleavage of 5α-bromo-3β-hydroxy-6β,19-oxidoandrostan-17-one results in the formation of 3β,19-dihydroxy-5-androsten-17-one diacetate. Lithium tri-t-butoxyaluminum hydride reduction then results in the preparation of 5-androstene-3β,17β,19- triol 3,19-diacetate. The 17β-hydroxy group can now be converted to an ether using standard procedures to form, for example, 17β-methoxy-5-androstene-3β,19-diol diacetate or 17β-(4'-tetrahydropyranyloxy)-5-androstene-3β,19-diol diacetate. A catalytic hydrogenation then furnishes the corresponding 5α-androstane. Basic hydrolysis subsequently cleaves the esters to form the free 17-ether diols. In this manner the compounds, 17β-methoxy-5α-androstane-3β,19- diol and 17β-(4'-tetrahydropyranyloxy)-5α-androstane-3β,19- diol can be prepared. Oxidation results in the formation of the corresponding diones. Etherification thereof furnishes the mixed triethers.

Sources & evidence

ORD record
ord-8b256dcd8b054bdd9a6e648d42cb8d65
Source dataset
uspto-grants-1978_01
Patent number
US04071625

Reaction notes

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