19-Hydroxytestosterone → Androst-4-en-17,19-diol-3-one

HRID 1197753Notes

Reaction equation

HRID 1197753 reaction equation
[CH3:1][C@@:2]12[C@@H:10]([OH:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH2:13][C:14]3[C@@:20]([CH2:21][OH:22])([C@H:5]1[CH2:4][CH2:3]2)[CH2:19][CH2:18][C:16](=[O:17])[CH:15]=3.C[C@]12CC[C@H]3[C@@H](CCC4[C@]3(C)CC[C@@H](O)C4)[C@@H]1CC=C2.[BH4-].[K+]>C(O)C>[CH3:1][C@:2]12[CH2:3][CH2:4][C@H:5]3[C@@H:6]([CH2:12][CH2:13][C:14]4[C@:20]3([CH2:21][OH:22])[CH2:19][CH2:18][C:16](=[O:17])[CH:15]=4)[C@@H:7]1[CH2:8][CH2:9][CH:10]2[OH:11]

Participants

5

Reactant 3

HCID 15096819-HydroxytestosteroneHCID 4192641Potassium borohydrideHCID 21117679Androsten-3alpha-ol

Product 1

HCID 22849351Androst-4-en-17,19-diol-3-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Also known as 19-Hydroxytestosterone, this compound is commercially available from Steraloids, Inc. Alternatively, 19-hydroxyandrost-4-en-3,17-dione (11) is treated with potassium borohydride (KBH4, a) in ethanol at -10° to 0° C. Aqueous work up is followed by extraction and purification to yield 19-hydroxytestosterone (12).

Workup

  1. customat -10° to 0° C
  2. extractionAqueous work up is followed by extraction and purification

Sources & evidence

ORD record
ord-46ba4dea4e15413688ceee04967c4ac2
Source dataset
uspto-grants-1994_01
Patent number
US05278141

Reaction notes

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