Androsta-4,16-dien-3-one → Androsta-4,16-dien-3alpha-ol

HRID 326982

Reaktionsgleichung

Reaktionsgleichung von HRID 326982
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH2:9][C:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C:12](=[O:20])[CH:11]=4)[C@@H:6]1[CH2:5][CH:4]=[CH:3]2.C(Cl)Cl.C(OCC)(=O)C>C1COCC1>[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH2:9][C:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C@@H:12]([OH:20])[CH:11]=4)[C@@H:6]1[CH2:5][CH:4]=[CH:3]2

Komponenten

4

Edukt 2

HCID 92979Androsta-4,16-dien-3-oneHCID 21226138Dichloromethane ethylacetate

Produkt 1

HCID 15858918Androsta-4,16-dien-3alpha-olAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

These syntheses are depicted in FIG. 2. Androsta-4,16-dien-3-one (4) was reduced at -55° with lithium tris(1,2-dimethylpropyl)hydridoborate in THF (c) as described for the preparation of 2 (FIG. 1). Chromatography on silica gel with CH2Cl2 /ethyl acetate 9:1 gave pure axial alcohol 15 (48%, yield) and pure equatorial alcohol 6 (48% yield). Analytical samples were further purified by recrystallization (from PE at -30° for 5, from cyclohexane at RT. for 6).

Aufarbeitung

  1. customas described for the preparation of 2 (FIG. 1)

Quellen und Nachweise

ORD-Eintrag
ord-99f8c5d0dfe24f7dbe4fb5c2bea6c64e
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05272134

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