androstane-3,6,17-triol synthesis
- Product Name:androstane-3,6,17-triol
- CAS Number:49644-04-4
- Molecular formula:C19H32O3
- Molecular Weight:308.46
53-43-0
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Yield:49644-04-4 70%
Reaction Conditions:
Stage #1: dehydroepiandrosteronewith borane-THF in tetrahydrofuran at -20 - 20; for 3 h;Inert atmosphere;
Stage #2: with sodium peroxoborate tetrahydrate in water at 20;
Steps:
1 Preparation of 5α-Androstane-3β,6α,17β-triol
A suitable intermediate for the synthesis of 6-α-3,17 androstanedione (2) was produced from dehydroepiandrosterone1 by hydroboration followed by oxidation as described in De Munari, et al. (J. Med. Chem., 2003,46(17):3644-54), the entire content of which is incorporated by reference herein. Briefly, a solution of dehydroepiandrosterone1 (5 g, 17.5 mmol, 1 eq.) in THF (85 mL) was stirred at -20 °C under Ar. Then, 1M BH3?THF complex in THFwas added to the stirred solution (44 mL, 44 mmol, 2.5 eq.), and stirring was continued at room temperature for 3 hours.H2O (85 mL) was cautiously added dropwise and followed by the dropwise addition of NaBO3?4H2O (5.4 g, 35 mmol, 2eq). After stirring at room temperature overnight, the mixture was filtered. The solid was washed with THF and thendiscarded. The liquors were saturated with NaCl and extracted with THF (3 3 40 mL). The combined organic extractswere dried over NaCl and Na2SO4, filtered, and evaporated to dryness. The crude 5α-Androstane-3β,6α,17β-triol 2product was crystallized from EtOAc/MeOH (2/1, 10 mL/g) to give a white solid (3.8 g, 70%).Spectroscopic data for 5α-Androstane-3β,6α,17β-triol 2:1H NMR (DMSO-d6) δ 4.44 (m, 1H, OH), 4.42 (m, 1H, OH), 4.24 (d, 1H, OH), 3.42 (dt, 1H, 16-Ha), 3.26 (m,1H, 3-H), 3.12 (m, 1H, 6-H), 0.72 (s, 3H, CH3), 0.60 (s, 3H, CH3). mp 232-234 °C.
References:
EP3805243,2021,A1 Location in patent:Paragraph 0147-0148; 0259-0262
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