Tetrahydrofuran → [1alpha,3beta]-1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]androst-5-en-17-one

HRID 434511

Reaktionsgleichung

Reaktionsgleichung von HRID 434511
[OH:1][C@@H:2]1[C@@:19]2([CH3:20])[C:6](=[CH:7][CH2:8][C@@H:9]3[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][CH2:12][C:13]2=[O:21])[CH2:5][C@@H:4]([OH:22])[CH2:3]1.[O:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1.[O:28]1[CH:33]=[CH:32][CH2:31][CH2:30][CH2:29]1.O.[C:35]1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[O:23]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:35]1[O:1][C@@H:2]1[C@@:19]2([CH3:20])[C:6](=[CH:7][CH2:8][C@@H:9]3[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][CH2:12][C:13]2=[O:21])[CH2:5][C@@H:4]([O:22][CH:33]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)[CH2:3]1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 80803,4-dihydro-2H-pyranHCID 1679551-HydroxydehydroepiandrosteroneHCID 521998p-Toluenesulfonic acid monohydrate

Produkt 1

HCID 13189253[1alpha,3beta]-1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]androst-5-en-17-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 0.91 g (0.0030 mol) of 1α,3β-dihydroxyandrost-5-en-17-one [R. M. Dodson, A. H. Goldkamp and R. D. Muir, J. Amer. Chem. Soc., 82, 4026 (1960)], 15 mL of tetrahydrofuran, 1.26 g (0.015 mol) of 3,4-dihydro-2H-pyran and 0.028 g of p-toluenesulfonic acid monohydrate was stirred at 25° for 18 hr. The mixture was diluted with methylene chloride. This solution was then washed with saturated aqueous sodium bicarbonate solution. The organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated to dryness to yield oily [1α,3β]-1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]androst-5-en-17-one, [α]D20 +34.3° (c 1, CHCl3).

Aufarbeitung

  1. washThis solution was then washed with saturated aqueous sodium bicarbonate solution
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-b31b37c0d51d44f59c5415282e5f735b
Quelldatensatz
uspto-grants-1983_08
Patentnummer
US04397847

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