21-Di[methylenebis(oxy)] 5α-Dihydrocortisol synthesis

4synthesis methods

Product Name:21-Di[methylenebis(oxy)] 5α-Dihydrocortisol
CAS Number:1056-08-2
Molecular formula:C23H34O6
Molecular Weight:406.51

807-05-6
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21-Di[methylenebis(oxy)] 5α-Dihydrocortisol

1056-08-2
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Yield:1056-08-2 51%

Reaction Conditions:

with ammonia;lithium in tetrahydrofuran at 20; for 0.333333 h;Birch Reduction;

Steps:

ii 17,20;20,21-Bismethylenedioxy-5α-pregnan-3-one (4)

To a solution of compound 3a (118 mg) in acetone (5 ml) was added Jones’ reagent (1 ml), and the mixture was stirred at room temperature for 30 min. After addition of MeOH to decompose the excess reagent, the organic solvent was evaporated under reduced pressure. The residue was diluted with EtOAc, washed with 5% NaHCO₃ and H₂O, dried over anhydrous Na₂SO₄, and evaporated to dryness. Purification of the product by column chromatography on silica gel with toluene-acetone (20:1, v/v) as an eluent and crystallization of a homogeneous effluent from CH₂Cl₂-MeOH gave 4 as colorless leaflets: yield, 111 mg (95%); mp 239-240 °C. (ii) To a blue colored suspension of metallic Li (200 mg) dispersed in liq. NH₃ (80 ml) was added a solution of the compound 1 (1.0 g) in tetrahydrofuran (15 ml), and the mixture was stirred at room temperature for 20 min with a dry-ice condenser. The reaction was quenched by adding an excess of NH₄Cl, and then most of NH₃ and solvent was evaporated. The residue, dissolved in H₂O, was acidified with 10% H₂SO₄ and extracted with EtOAc. The combined extract was washed with saturated brine, dried over anhydrous MgSO₄, and evaporated to dryness under reduced pressure. The crude product was subjected to column chromatography on silica gel with n-hexane-EtOAc (65:35, v/v) as an eluent. Crystallization of a homogeneous effluent from CH₂Cl₂-MeOH gave 4 as colorless leaflets: yield, 594 mg (59%); mp 239-240 °C.

References:

Mitamura, Kuniko;Mabuchi, Takayuki;Nagae, Kaori;Nakajima, Masataka;Matsumoto, Rina;Fujioka, Sachi;Sato, Kanta;Satoh, Rika;Iida, Takashi;Ogawa, Shoujiro;Hofmann, Alan F.;Ikegawa, Shigeo [Steroids,2012,vol. 77,# 13,p. 1423 - 1437]

Pregn-4-ene-3,11-dione, 17,20:20,21-bis[methylenebis(oxy)]-

3607-68-9
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1056-08-2
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References

52248-40-5 Synthesis

Pregn-5-ene-3,11-dione, 17,20:20,21-bis[methylenebis(oxy)]-, cyclic 3-(1,2-ethanediyl acetal)

52248-40-5
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1056-08-2
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References

5α-Pregnane-3,6,11-trione, 17,20:20,21-bis(methylenedioxy)-, cyclic 3-(ethylene acetal) (6CI,7CI)

107157-45-9
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1056-08-2
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References