Dehydroepiandrosterone → 5beta,6beta-Epoxyandrostan-17-one

HRID 42101

Reaktionsgleichung

Reaktionsgleichung von HRID 42101
O[C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C:11]2=[O:21])[CH2:3]1.C1C=C(Cl)C=C(C(OO)=[O:30])C=1.[O-:33]S([O-])=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[O:30]1[C@H:5]2[CH2:6][C@@H:7]3[C@@H:16]([C@@:17]4([CH3:20])[CH2:18][CH2:19][CH2:2][CH2:3][C@:4]124)[CH2:15][CH2:14][C@@:12]1([CH3:13])[C@H:8]3[CH2:9][CH2:10][C:11]1=[O:21].[O:33]1[C@@H:5]2[CH2:6][C@@H:7]3[C@@H:16]([C@@:17]4([CH3:20])[CH2:18][CH2:19][CH2:2][CH2:3][C@@:4]124)[CH2:15][CH2:14][C@@:12]1([CH3:13])[C@H:8]3[CH2:9][CH2:10][C:11]1=[O:21]

Komponenten

7

Edukt 4

HCID 5881DehydroepiandrosteroneHCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium Bicarbonate

Produkt 2

HCID 141350635beta,6beta-Epoxyandrostan-17-oneHCID 141350645alpha,6alpha-Epoxyandrostan-17-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 3β-hydroxyandrost-5-en-17-one (0.81 g) in CH2Cl2 (7.4 mL) cooled at 0° C., a solution of mCPBA (0.77 mg) in CH2Cl2 (14 mL) was added dropwise. After 0.5 h at 0° C. and 0.5 h at room temperature, a 10% Na2SO3 aqueous solution was added. The mixture was neutralized by addition of 5% aqueous NaHCO3 solution and extracted with CH2Cl2 (3×100 mL). The combined organic extracts were washed with H2O, dried over Na2SO4, and evaporated to dryness to give 5α,6α-epoxyandrostan-17-one and 5β,6β-epoxyandrostan-17-one as a white foam (1/1 mixture; 1.24 g, 97%). 1H-NMR (300 MHz, acetone-d6, ppm from TMS): 3β-hydroxy-5α,6α-epoxyandrostan-17-one δ 3.26 (1H, d), 2.96 (1H, d), 2.70-1.12 (18H, m), 1.36 (3H, s), 0.83 (3H, s); 3β-hydroxy-5α,6β-epoxyandrostan-17-one: δ 2.98 (1H, d), 2.93 (1H, d), 2.71-1.13 (18H, m), 1.06 (3H, s), 0.84 (3H, s).

Aufarbeitung

  1. extractionextracted with CH2Cl2 (3×100 mL)
  2. washThe combined organic extracts were washed with H2O
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-2e784977854e4c5fa8c99135fb7e0db7
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536160B2

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