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

HRID 617102

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

Reactant 3

HCID 962Water

HCID 1049Pyridine

HCID 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

filtrationcrystals are filtered
customdried in vacuo

Sources & evidence

ORD record: ord-2af5f12075e44800b7b8f66185393a18
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05948434

Linked notes

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