Acetic Acid → 19-Methoxy-androst-4-ene-3beta,17beta-diol

HRID 1733075Notes

Reaction equation

[CH3:1][O:2][CH2:3][C@@:4]12[C@@H:21]3[C@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C:16](=[O:22])[CH2:15][CH2:14]4)[CH2:11][CH2:10][C:9]1=[CH:8][C:7](=[O:23])[CH2:6][CH2:5]2.[BH4-].[Na+].C(O)(=O)C>CO.O>[CH3:1][O:2][CH2:3][C@@:4]12[C@@H:21]3[C@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C@@H:16]([OH:22])[CH2:15][CH2:14]4)[CH2:11][CH2:10][C:9]1=[CH:8][C@@H:7]([OH:23])[CH2:6][CH2:5]2

Participants

Conditions

Temperature: 0 °C

Procedure

19-Methoxyandrost-4-ene-3,17-dione is dissolved in methanol and the solution cooled to 0° C. Sodium borohydride is added over a period of fifteen minutes and stirring continued for an additional two hours. The solution is poured into water containing a few drops of acetic acid. The white precipitate which forms is collected by filtration, dried and crystallized from acetone to yield the desired 19-methoxy-androst-4-ene-3β,17β-diol.

Workup

filtrationThe white precipitate which forms is collected by filtration
customdried
customcrystallized from acetone

Sources & evidence

ORD record: ord-06a80b17f2b043328d7706c6280c28de
Source dataset: uspto-grants-1980_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04239681

Reaction notes

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