Dimethoxymethane → 17beta-Acetoxy-3beta-methoxymethoxy-1alpha-methyl-17alpha-n-propyl-5alpha-androstane

HRID 637647

Reaktionsgleichung

Reaktionsgleichung von HRID 637647
[C:1]([O:4][C@@:5]1([CH2:26][CH2:27][CH3:28])[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C@H:14]([CH2:15][C@@H:16]([OH:25])[CH2:17][C@@H:18]1[CH3:24])[CH2:13][CH2:12]3)(=[O:3])[CH3:2].[CH3:29][O:30][CH2:31]OC.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>ClCCl>[C:1]([O:4][C@@:5]1([CH2:26][CH2:27][CH3:28])[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C@H:14]([CH2:15][C@@H:16]([O:25][CH2:29][O:30][CH3:31])[CH2:17][C@@H:18]1[CH3:24])[CH2:13][CH2:12]3)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 8020DimethoxymethaneHCID 14812Phosphorus oxide (P4O10)HCID 7036026117beta-Acetoxy-1alpha-methyl-17alpha-n-propyl-5alpha-androstan-3beta-ol

Produkt 1

HCID 7036024817beta-Acetoxy-3beta-methoxymethoxy-1alpha-methyl-17alpha-n-propyl-5alpha-androstane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

400 mg of 17β-acetoxy-1α-methyl-17α-n-propyl-5α-androstan-3β-ol is combined in 2.8 ml of absolute dichloromethane and 1.8 ml of formaldehyde dimethylacetal with a mixture of 600 mg of kieselguhr W 20 and 300 mg of phosphorus pentoxide and stirred for 45 minutes at room temperature. The mixture is vacuum-filtered from the insoluble components and washed with dichloromethane containing 3-5% triethylamine. The crude product obtained after evaporation is chromatographed on silica gel, thus producing 280 mg of 17β-acetoxy-3β-methoxymethoxy-1α-methyl-17α-n-propyl-5α-androstane.

Aufarbeitung

  1. filtrationThe mixture is vacuum-filtered from the insoluble components
  2. washwashed with dichloromethane containing 3-5% triethylamine
  3. customThe crude product obtained
  4. customafter evaporation
  5. customis chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-83100f2fd2e2449e86361a6d6023b29a
Quelldatensatz
uspto-grants-1985_12
Patentnummer
US04558041

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