Water → (2beta,3alpha,5alpha,17beta)-3-Hydroxy-2-(2,2-dimethyl-4-morpholinyl)androstan-11-one-17-carbonitrile

HRID 233526Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 233526
Cl.[CH3:2][C:3]1([CH3:9])[O:8][CH2:7][CH2:6][NH:5][CH2:4]1.[OH-].[Na+].[O:12]1[C@H:14]2[CH2:15][C@H:16]3[C@:29]([CH3:31])([CH2:30][C@@H:13]12)[C@@H:28]1[C@H:19]([C@H:20]2[C@@:24]([CH2:26][C:27]1=[O:32])([CH3:25])[C@@H:23]([C:33]#[N:34])[CH2:22][CH2:21]2)[CH2:18][CH2:17]3.O>C(O)CO>[OH:12][C@@H:14]1[C@@H:13]([N:5]2[CH2:6][CH2:7][O:8][C:3]([CH3:9])([CH3:2])[CH2:4]2)[CH2:30][C@@:29]2([CH3:31])[C@@H:16]([CH2:17][CH2:18][C@@H:19]3[C@@H:28]2[C:27](=[O:32])[CH2:26][C@@:24]2([CH3:25])[C@H:20]3[CH2:21][CH2:22][C@@H:23]2[C:33]#[N:34])[CH2:15]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 220368882,2-Dimethylmorpholine hydrochlorideHCID 8673313717beta-Cyano-2alpha,3alpha-epoxy-5alpha-androstan-11-one

Produkt 1

HCID 22868795(2beta,3alpha,5alpha,17beta)-3-Hydroxy-2-(2,2-dimethyl-4-morpholinyl)androstan-11-one-17-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 174Ethylene GlycolLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

2,2-Dimethylmorpholine hydrochloride (9.67 g) and sodium hydroxide (2.55 g) were added to a mixture (4:1) of (2α,3α,5α,17β)-2,3-epoxyandrostan-11-one-17-carbonitrile and its 3α,4α-epoxy isomer (5.0 g) (British patent 1,434,919) in 1,2-ethanediol (50 ml) and the mixture was heated in an atmosphere of nitrogen at 120° C. for 19 h and then at 150° C. for 4.5 h. The reaction mixture was poured into water (500 ml) and the precipitated solid was filtered off and dissolved in dichloromethane. After washing the solution with water and drying over sodium sulfate, the solvent was removed under reduced pressure and the residue (6.9 g) was chromatographed on silica gel. The purified product (4.3 g) was sequentially crystallised from ethanol and acetone-diethyl ether to give (2β,3α,5α,17β)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)androstan-11-one-17-carbonitrile (2.37 g). m.p. 206°-210° C.; [α]D +122.9° (c 0.8).

Aufarbeitung

  1. filtrationthe precipitated solid was filtered off
  2. dissolutiondissolved in dichloromethane
  3. washAfter washing the solution with water
  4. dry with materialdrying over sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customthe residue (6.9 g) was chromatographed on silica gel
  7. customThe purified product (4.3 g) was sequentially crystallised from ethanol and acetone-diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-f4f88aa1985a4d4bba0a7bfa29838480
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05593983

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