Water → 2beta-(4-Morpholinyl)-16beta-(1-pyrrolidinyl)-5alpha-androstane-3alpha,17beta-diol

HRID 329955

Reaktionsgleichung

Reaktionsgleichung von HRID 329955
[OH2:1].[O:2]1[C@H:4]2[CH2:5][C@H:6]3[C@:19]([CH3:21])([CH2:20][C@@H:3]12)[C@@H:18]1[C@H:9]([C@H:10]2[C@@:14]([CH2:16][CH2:17]1)([CH3:15])[C@@H:13]([OH:22])[C@@H:12]([N:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1)[CH2:11]2)[CH2:8][CH2:7]3>N1CCOCC1>[N:23]1([C@H:3]2[CH2:20][C@@:19]3([CH3:21])[C@@H:6]([CH2:7][CH2:8][C@@H:9]4[C@@H:18]3[CH2:17][CH2:16][C@@:14]3([CH3:15])[C@H:10]4[CH2:11][C@H:12]([N:23]4[CH2:27][CH2:26][CH2:25][CH2:24]4)[C@@H:13]3[OH:22])[CH2:5][C@@H:4]2[OH:2])[CH2:24][CH2:25][O:1][CH2:11][CH2:12]1

Komponenten

4

Edukt 2

HCID 962WaterHCID 160638722Alpha,3alpha-epoxy-16beta-(1-pyrrolidinyl)-5alpha-androstan-17beta-OL

Produkt 1

HCID 160638732beta-(4-Morpholinyl)-16beta-(1-pyrrolidinyl)-5alpha-androstane-3alpha,17beta-diol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8083MorpholineLösungsmittel

Versuchsvorschrift

Water (50 ml) was added to a solution of (2α,3α,5α,16β,17β)2,3-epoxy-16-(1-pyrrolidinyl)-androstan-17-ol (85.2 g) in morpholine (500 ml) and the reaction mixture was heated at reflux temperature for 3 d. Evaporation of the reaction mixture gave a crude product, which was crystallised from acetone. Recrystallisation from methanol gave pure (2β,3α,5α,16β,17β)-2(4-morpholinyl)-16-(1-pyrrolidinyl)-androstane-3,17-diol (71.2 g), m.p. 212°-219° C.; [α]D20 =+87.9° (c 1.02 in CHCl3).

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux temperature for 3 d
  3. customEvaporation of the reaction mixture
  4. customgave a crude product, which
  5. customwas crystallised from acetone
  6. customRecrystallisation from methanol

Quellen und Nachweise

ORD-Eintrag
ord-a8f39742c77844b59ce9511ad4f8a876
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04894369

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