Methylprednisolone → 6alpha-Methylhydrocortisone

HRID 2197393Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2197393
[OH:1][C@@H:2]1[C@H:18]2[C@@H:9]([CH2:10][C@H:11]([CH3:21])[C:12]3[C@:17]2([CH3:19])[CH:16]=[CH:15][C:14](=[O:20])[CH:13]=3)[C@H:8]2[C@@:4]([CH3:27])([C@@:5]([OH:26])([C:22](=[O:25])[CH2:23][OH:24])[CH2:6][CH2:7]2)[CH2:3]1.[H][H]>CCOC(C)=O.C(O)C>[OH:1][C@@H:2]1[C@H:18]2[C@@H:9]([CH2:10][C@H:11]([CH3:21])[C:12]3[C@:17]2([CH3:19])[CH2:16][CH2:15][C:14](=[O:20])[CH:13]=3)[C@H:8]2[C@@:4]([CH3:27])([C@@:5]([OH:26])([C:22](=[O:25])[CH2:23][OH:24])[CH2:6][CH2:7]2)[CH2:3]1

Komponenten

5

Edukt 2

HCID 6741MethylprednisoloneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 1021476alpha-MethylhydrocortisoneAusbeute 94,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In a 250 mL round-bottomed flask was suspended (6S,8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-6,10,13-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one (6α-Methylprednisolon, 4.3 g, 11.48 mmol) in EtOAc (80 mL) and the reaction mixture was diluted with ethanol (20.0 mL). Tris(triphenylphosphine)rhodium(I)chloride (Wilkinson's catalyst, 1 g, 1.08 mmol) was added together with a magnetic stirrer bar and the flask was vigorously stirred in a hydrogen atmosphere (1 atm) at room temperature for 1 week. The reaction mixture was filtered through a glass filter funnel and the filtrate was concentrated in vacuo to yield 4.07 g of the desired compound as a light brown solid which was used in the next step without any further purification. APCI-MS m/z: 377 [MH+].

Aufarbeitung

  1. customIn a 250 mL round-bottomed flask was suspended
  2. filtrationThe reaction mixture was filtered through a glass
  3. filtrationfilter funnel
  4. concentrationthe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4c6e88d4b42f4559993ff64ccdad5539
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338587B2

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