Triethylamine → 17beta-n-Butoxycarbonyl-3alpha-hydroxy-5alpha-androstan-11-one

HRID 267617Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 267617
[OH:1][C@@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[C:15](=[O:21])[CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:22]([OH:24])=[O:23])[CH2:3]1.C(N(CC)CC)C.[CH2:32](I)[CH2:33][CH2:34][CH3:35]>CC(C)=O>[CH2:32]([O:23][C:22]([C@H:11]1[CH2:10][CH2:9][C@H:8]2[C@H:7]3[C@H:16]([C:15](=[O:21])[CH2:14][C@:12]12[CH3:13])[C@:17]1([CH3:20])[C@H:4]([CH2:3][C@H:2]([OH:1])[CH2:19][CH2:18]1)[CH2:5][CH2:6]3)=[O:24])[CH2:33][CH2:34][CH3:35]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10962Butyl iodideHCID 227882653alpha-Hydroxy-5alpha-androstan-11-one 17beta-carboxylic acid

Produkt 1

HCID 2278825217beta-n-Butoxycarbonyl-3alpha-hydroxy-5alpha-androstan-11-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A solution of 3α-hydroxy-11-oxo-5α-androstane-17β-carboxylic acid (521 mg.) in dry acetone (50 ml.) was refluxed with triethylamine (1.04 ml.) and n-butyl iodide (0.87 ml.) for 16 hours. The mixture was evaporated to a residue which was dissolved in chloroform, washed with water, dried (Na2SO4) and evaporated to a foam (534 mg.). A solution of the foam in ether was washed with saturated sodium bicarbonate solution and with water, dried (Na2SO4) and evaporated to give title compound (443 mg.) as a white foam, [α]D + 51°.

Aufarbeitung

  1. customThe mixture was evaporated to a residue which
  2. dissolutionwas dissolved in chloroform
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated to a foam (534 mg.)
  6. washA solution of the foam in ether was washed with saturated sodium bicarbonate solution and with water
  7. dry with materialdried (Na2SO4)
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-415089cbab4f467e921a99664cf6ae26
Quelldatensatz
uspto-grants-1976_03
Patentnummer
US03943124

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