ChemicalBook CAS DataBase List ALLOPREGNANOLONE

ALLOPREGNANOLONE synthesis

14synthesis methods

Product Name:ALLOPREGNANOLONE
CAS Number:516-55-2
Molecular formula:C21H34O2
Molecular Weight:318.49

145-13-1 Synthesis

145-13-1
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$28.00/500mg

516-55-2
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$20.00/250mg

Yield:516-55-2 100%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen;glacial acetic acid in tetrahydrofuran at 60; under 3102.97 Torr;

Steps:

2 Referring to Route 1, Synthesis of 1-((3S,8R,10S,13S,14S,17S)-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethenone:

(pregnenolone) Pregnenolone (3.17 g, 10 mmol) was dissolved in 30 mL of THF and 5 mL of acetic acid. To it, 10% Pd/C (0.3 g) was added. The resulting mixture was shaken under 60 psi hydrogen at 60 °C overnight. It was filtered through a Celite pad and concentrated to give 3.2 g of the desired product (100%). ¹H NMR (400 MHz, CDC13) d 3.58 (tt, J = 11.0, 4.8 Hz, 1H), 2.50 (t, J = 9.0 Hz, 1H), 2.19 - 2.11 (m, 2H), 2.09 (s, 3H), 2.06 - 1.93 (m, 2H), 1.85 - 1.75 (m, 1H), 1.74 - 1.50 (m, 6H), 1.47 - 1.04 (m, 9H), 1.04 - 0.82 (m, 2H), 0.79 (s, 3H), 0.72 - 0.61 (m, 1H), 0.58 (d, J = 2.4 Hz, 3H).

References:

WO2019/209850,2019,A1 Location in patent:Paragraph 0103; 0105; 0106

1162-53-4 Synthesis