Triethylamine → 3alpha-Hydroxy-21-(pyrid-4-yloxy)-5beta-pregnan-20-one

HRID 1837125Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1837125
Br[CH2:2][C:3](=[O:24])[C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([CH2:19][CH2:20]2)[C@:16]2([CH3:17])[C@@H:11]([CH2:12][C@H:13]([OH:23])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1.[OH:25][C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1.C(N(CC)CC)C>C1COCC1>[OH:23][C@@H:13]1[CH2:14][CH2:15][C@@:16]2([CH3:17])[C@H:11]([CH2:10][CH2:9][C@@H:8]3[C@@H:18]2[CH2:19][CH2:20][C@@:21]2([CH3:22])[C@H:7]3[CH2:6][CH2:5][C@@H:4]2[C:3](=[O:24])[CH2:2][O:25][C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)[CH2:12]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 8675425121-Bromo-3alpha-hydroxy-5beta-pregnan-20-oneHCID 178418642HCID 178418642, Verbindung

Produkt 1

HCID 213103243alpha-Hydroxy-21-(pyrid-4-yloxy)-5beta-pregnan-20-oneAusbeute 7,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 21-bromo-3α-hydroxy-5β-pregnan-20-one (500 mg, 1.26 mmol), 4-hydroxypyridine (144 mg, 1.51 mmol), and triethyl amine (200 μL) in 10 mL of THF was heated under reflux for 4 h. The mixture was cooled to room temperature and partitioned between EtOAc and water. The organic layer was washed with sat. aq. NaCl, dried with MgSO4 and concentrated in vacua. The crude residue was subjected to flash column chromatography. Elution with 50% acetone in CH2Cl2 yielded 3α-hydroxy-21-(pyrid-4-yloxy)-5β-pregnan-20-one (40 mg) as an oily solid; TLC Rf (acetone:CH2Cl2 1:1)=0.28.

Aufarbeitung

  1. temperatureunder reflux for 4 h
  2. custompartitioned between EtOAc and water
  3. washThe organic layer was washed with sat. aq. NaCl
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated in vacua
  6. washElution with 50% acetone in CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-f93652a3deed499e9b7db2fd0cf50d20
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06780853B1

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