Water → 3beta-Acetoxyandrost-5-en-17-one

HRID 1956133Notes

Reaction equation

HRID 1956133 reaction equation
[CH3:1][C@@:2]12[C:10](=[O:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH:13]=[C:14]3[CH2:19][C@@H:18]([OH:20])[CH2:17][CH2:16][C@:15]3([CH3:21])[C@H:5]1[CH2:4][CH2:3]2.[OH2:22].N1[CH:28]=[CH:27]C=CC=1>>[C:27]([O:20][C@H:18]1[CH2:17][CH2:16][C@@:15]2([CH3:21])[C:14](=[CH:13][CH2:12][C@@H:6]3[C@@H:5]2[CH2:4][CH2:3][C@@:2]2([CH3:1])[C@H:7]3[CH2:8][CH2:9][C:10]2=[O:11])[CH2:19]1)(=[O:22])[CH3:28]

Participants

4

Reactant 3

HCID 962WaterHCID 1049PyridineHCID 5881Dehydroepiandrosterone

Product 1

HCID 147093beta-Acetoxyandrost-5-en-17-one

Procedure

Dehydroepiandrosterone (2.88 g, 10 mmol) is dissolved in a mixture (100 ml) of anhydride acetic and pyridine (1:1 v/v) and left at room temperature for 16 h. The mixture is then poured carefully into iced water and after 16 h, crystals are filtered and dried in vacuo.

Workup

  1. filtrationcrystals are filtered
  2. customdried in vacuo

Sources & evidence

ORD record
ord-830b07aec69f441094556cc539bb27fe
Source dataset
uspto-grants-1998_07
Patent number
US05780460

Reaction notes

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