ChemicalBook CAS DataBase List Androstenedione

Androstenedione synthesis

12synthesis methods

Product Name:Androstenedione
CAS Number:63-05-8
Molecular formula:C19H26O2
Molecular Weight:286.41

58-22-0 Synthesis

58-22-0
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$21.00/1mg

63-05-8
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$32.00/1mg

Yield:63-05-8 100%

Reaction Conditions:

with Jones reagent in propan-2-one at 0;Jones Oxidation;

Steps:

2

EXAMPLE 2Synthesis of HC1 salt of 10, 13-Dimethyl-l ,6,7,8,9, 10, l l , 12, 13,14, 15, 16-dodecahydro- cyclopenta[a]phenanthrene-3, 17-dione 3-[0-(2-amino-ethyl)-o xime (Hydrochloride salt Compound (12))HC1 salt of Compound (12)Preparation of HC1 salt of Compound (12)To a solution of testosterone (1.7 mmol) in acetone (10 mL) was added an excess of Jones reagent (~2 mL) dropwise, maintaining the temperature at 0 °C. After completion of the reaction (monitored by TLC), iPrOH was added and, after further 10 min, the suspension was filtered through a short plug of silica, washed with acetone and the filtrate evaporated to dryness. The residue was treated with H₂0 and extracted with EtOAc (3x25 mL). The combined organic extracts were washed with H₂0, 5% aqueous NaHCC>3 solution, H₂0, dried over Na₂S0₄ and evaporated to dryness to give the desired product as a white solid. The product was subjected to a short silica column to afford compound al as a white solid in quantitative yield. 'H-NMR (600 MHz, CDC1₃): δ 5.75 (s, 1H) 2.52 - 1.22 (m, 17H), 1.21 (s, 3H), 1.15 - 0.95 (m, 2H) 0.92 (s, 3H).

References:

WO2011/29639,2011,A2 Location in patent:Page/Page column 104-105