3alpha-Azido-5alpha-pregnan-20-one → 3alpha-Azido-21-bromo-5alpha-pregnan-20-one

HRID 1829637Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1829637
[N:1]([C@@H:4]1[CH2:23][CH2:22][C@@:21]2([CH3:24])[C@@H:6]([CH2:7][CH2:8][C@@H:9]3[C@@H:20]2[CH2:19][CH2:18][C@@:17]2([CH3:25])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C:14](=[O:16])[CH3:15])[CH2:5]1)=[N+:2]=[N-:3].C1C=C[NH+]=CC=1.[Br:32][Br-]Br>C(O)C.C(Cl)(Cl)Cl.ClCCl>[N:1]([C@@H:4]1[CH2:23][CH2:22][C@@:21]2([CH3:24])[C@@H:6]([CH2:7][CH2:8][C@@H:9]3[C@@H:20]2[CH2:19][CH2:18][C@@:17]2([CH3:25])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C:14](=[O:16])[CH2:15][Br:32])[CH2:5]1)=[N+:2]=[N-:3]

Komponenten

5

Edukt 1

HCID 99460603alpha-Azido-5alpha-pregnan-20-one

Produkt 1

HCID 866001863alpha-Azido-21-bromo-5alpha-pregnan-20-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 3α-azido-5α-pregnan-20-one (51.5 mg, 0.15 mmol) in absolute ethanol (3 mL) and chloroform (3 mL) was added pyridinium bromide perbromide (143 mg, 0.44 mmol) and the resulting mixture was heated at 50° C. for 45 min. Subsequently the mixture was diluted with dichloromethane and the organic layer was washed with water, brine and dried (Na2SO4). Evaporation of the solvent in vacuo and purification of the residue using flash column chromatography and petroleum ether/ethyl acetate 90/10 as elution solvent afforded the compound named above.

Aufarbeitung

  1. washthe organic layer was washed with water, brine
  2. dry with materialdried (Na2SO4)
  3. customEvaporation of the solvent
  4. customin vacuo and purification of the residue
  5. washas elution solvent
  6. customafforded the compound

Quellen und Nachweise

ORD-Eintrag
ord-fd6b8733b58441ce9dbc3401d2248a21
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07064116B2

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