Ammonium Chloride → 25-Hydroxy-7-dehydrocholesterol

HRID 2419197

Reaktionsgleichung

Reaktionsgleichung von HRID 2419197
[CH3:1][C@@H:2]([C@@H:10]1[C@@:14]2([CH3:29])[CH2:15][CH2:16][CH2:17]/[C:18](=[CH:19]\[CH:20]=[C:21]3\[CH2:22][C@@H:23]([OH:28])[CH2:24][CH2:25][C:26]\3=[CH2:27])/[C@@H:13]2[CH2:12][CH2:11]1)[CH2:3][CH2:4][CH2:5][C:6]([OH:9])([CH3:8])[CH3:7].C[Mg]Br.[Cl-].[NH4+]>C1C=CC=CC=1>[CH3:8][C:6]([OH:9])([CH2:5][CH2:4][CH2:3][C@H:2]([C@@H:10]1[C@:14]2([CH3:29])[C@H:13]([C:18]3[C@H:17]([CH2:16][CH2:15]2)[C@:26]2([CH3:27])[C:21]([CH2:22][C@@H:23]([OH:28])[CH2:24][CH2:25]2)=[CH:20][CH:19]=3)[CH2:12][CH2:11]1)[CH3:1])[CH3:7]

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 528373125-Hydroxyvitamin D3HCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 990898325-Hydroxy-7-dehydrocholesterol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

As noted above, the 3β-hydroxy-27-norcholest-5,7-dien-25-one prepared in accordance with the process of the instant invention is readily converted by techniques well-known in the art into 25-hydroxyvitamin D3. Thus, as described in the previously cited RECUEIL reference, 3β-hydroxy-27-norcholest-5,7-dien-25-one in dry benzene may be treated with methyl magnesium bromide at about 5° C. The reaction mixture is stirred for 8 - 18 hours and then is worked up by the addition of an aqueous solution of ammonium chloride. The cholest-5,7-diene-3β,25-diol so produced is crystallized from successively tetrahydrofuran-diisopropyl ether and tetrahydrofuran-ethyl acetate.

Aufarbeitung

  1. customprepared in accordance with the process of the instant invention

Quellen und Nachweise

ORD-Eintrag
ord-32a109ec59e74de088aeef4d9b78f0bf
Quelldatensatz
uspto-grants-1978_08
Patentnummer
US04105660

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