ChemicalBook CAS DataBase List (16α-bromine)-3α-Dehydroepiandrosterone

(16α-bromine)-3α-Dehydroepiandrosterone synthesis

5synthesis methods

Product Name:(16α-bromine)-3α-Dehydroepiandrosterone
CAS Number:1093-91-0
Molecular formula:C19H27BrO2
Molecular Weight:367.3205

53-43-0 Synthesis

53-43-0
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1093-91-0
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Yield:1093-91-0 97%

Reaction Conditions:

with copper(ll) bromide in methanol at 70; for 12 h;

Steps:

2.1. General procedure for the synthesis of compounds 3, 4

General procedure: A mixture of dehydroepiandrosterone 1 (5.00 g, 17.40 mmol) and CuBr2 (11.50 g,51.60 mmol, 3.00 eq.) in methanol (100 mL) was stirred at 70 for 12 h andmonitored by TLC. After cooling, the inorganic salt was filtered off. The filtrate wasevaporated in vacuo. The residue was dissolved in DCM (100 mL), then washed with brine(20 mL × 3). The organic phase was separated and dried over anhydrous Na2SO4. Then thesolvent was evaporated in vacuo and the crude product was purified by flash columnchromatography to give the title compound 3 as a white solid (6.20 g, 97%).

References:

Zhao, Jian-Wei;Wu, Zeng-Hui;Guo, Jia-Wen;Huang, Ming-Jie;You, Ya-Zhen;Liu, Hong-Min;Huang, Li-Hua [European Journal of Medicinal Chemistry,2019,vol. 181,art. no. 111520] Location in patent:supporting information