17α-[3-Hydroxypropyl]-6β,7β:15β,16β-diMethylen-5β-androstan-5,17β-ol-3-one synthesis
- Product Name:17α-[3-Hydroxypropyl]-6β,7β:15β,16β-diMethylen-5β-androstan-5,17β-ol-3-one
- CAS Number:1357252-81-3
- Molecular formula:C24H36O4
- Molecular Weight:388.54
1248589-65-2
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1357252-81-3
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Yield:1357252-81-3 100%
Reaction Conditions:
with tetrabutyl ammonium fluoride in tetrahydrofuran at 0 - 20; for 4 h;Product distribution / selectivity;
Steps:
10
Example 10 17α-(3-hydroxypropyl)-6β,7β,15β,16β-dimethylen-5β-androstan-5,17β-ol-3-one (7); [Show Image]; 17α-[3-(tert-Butyl-dimethylsilanyloxy)propyl]-6β,7β,15β,16β-dimethylen-5p-androstan-5,17p-ol-3-one 6b obtained according to Example 9 (5.5 g, 0.011 mol) is dissolved in tetrahydrofuran and cooled to 0°C. Tetrabutylammonium fluoride trihydrate is added in three portions (1.74 g, 0.006 mol) over 2 hours; the mixture is then stirred at 0°C for two additional hours and analyzed by TLC. After allowing the reaction to reach room temperature, ethyl acetate (50 mL) and saturated sodium bicarbonate solution (50 mL) are added and the phases are separated. The aqueous layer is extracted with ethyl acetate (30 mL) and the combined organic phases are washed with brine (50 mL). After separation the organic solvent is removed under reduced pressure at 45°C affording the product 7 as a pale yellow solid (5.4 g, quantitative) which is used in the following step without further purification. Analytical data correspond to the ones reported in Example 7.
References:
EP2415778,2012,A1 Location in patent:Page/Page column 15-16
1104734-52-2
1 suppliers
inquiry
1357252-81-3
12 suppliers
$165.00/10mg