3beta-Benzyloxy-5-androsten-17-one → 3beta-Methyl-5alpha-androstan-17-one

HRID 1199153Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1199153
O([C@:3]12[CH2:20][C@@H:19](O)[CH2:18][CH2:17][C@:16]1([CH3:22])[C@@H:15]1[C@H:6]([C@H:7]3[C@@:11]([CH2:13][CH2:14]1)([CH3:12])[C:10](=[O:23])[CH2:9][CH2:8]3)[CH:5]=[CH:4]2)O.[CH2:24](O[C@H]1CC[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CCC2=O)C1)C1C=CC=CC=1.[H][H]>C(O)(=O)C.[Pd]>[CH3:24][C@H:19]1[CH2:18][CH2:17][C@@:16]2([CH3:22])[C@@H:3]([CH2:4][CH2:5][C@@H:6]3[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]3[CH2:8][CH2:9][C:10]2=[O:23])[CH2:20]1

Komponenten

6

Edukt 3

HCID 537649083beta-Benzyloxy-5-androsten-17-one2×HCID 566283895alpha-Hydroperoxy-3beta-hydroxyandrost-6-en-17oneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 186376273beta-Methyl-5alpha-androstan-17-oneAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Firstly an example of catalytic hydrogenation for the synthesis of 5α-androstanes from androst-5-enes is the synthesis of 3β-methyl-5α-androstan-17-one 2 from 3β-methylandrost-5-en-17-one 1. 3β-Methylandrost-5-en-17-one 1 (400 mg), prepared as described previously was dissolved in glacial acetic acid (80 ml). Palladium on carbon (10%, 100 mg) was added and the solution maintained under an atmosphere of hydrogen. When hydrogen uptake ceased, the solution was filtered through celite and evaporated to give solid which was recrystallized from methanol to yield 3β-methyl-5α-androstan-17-one, 2, (320 mg, 80% yield). MP 107°-108° C., 1H NMR (CDCl3)δ 0.86 (d, 3H, J-5Hz, methyl at C-3), 0.85 (s, 3H, C-19 Me), 0.79 (s, 3H, C-18 Me). ##STR53##

Aufarbeitung

  1. temperaturethe solution maintained under an atmosphere of hydrogen
  2. filtrationthe solution was filtered through celite
  3. customevaporated
  4. customto give solid which
  5. customwas recrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-1a9350ff364740d2ae33845dd04e1000
Quelldatensatz
uspto-grants-1990_02
Patentnummer
US04898694

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