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Hydrochloric Acid → 7alpha-(9-Methylaminononyl)oestra-1,3,5(10)-triene-3,17beta-diol

HRID 543017
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 543017
[OH:1][C:2]1[CH:19]=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C@@H:11]([OH:20])[CH2:10][CH2:9]4)[C@H:6]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([NH:31][CH3:32])=O)[CH2:5][C:4]=2[CH:3]=1.B.Cl>O1CCCC1>[CH3:32][NH:31][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][C@@H:6]1[CH2:5][C:4]2[CH:3]=[C:2]([OH:1])[CH:19]=[CH:18][C:17]=2[C@@H:16]2[C@@H:7]1[C@H:8]1[C@@:12]([CH2:14][CH2:15]2)([CH3:13])[C@@H:11]([OH:20])[CH2:10][CH2:9]1
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Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 704467659-(3,17beta-dihydroxyoestra-1,3,5(10)-trien-7alpha-yl)-N-methyl-nonanamide

Produkt 1

HCID 543355367alpha-(9-Methylaminononyl)oestra-1,3,5(10)-triene-3,17beta-diol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 9-(3,17β-dihydroxyoestra-1,3,5(10)-trien-7α-yl)-N-methylnonanamide (Example 27; 0.047 g.) and a molar solution of borane in tetrahydrofuran (5 ml.) was heated under reflux for 2 hours, cooled and concentrated aqueous hydrochloric acid (2 ml.) was added. The tetrahydrofuran was removed by evaporation and the residue was basified with aqueous 5N-sodium hydroxide solution and extracted three times with ethyl acetate (10 ml. each time). The combined extracts were washed with water (2 ml.), dried and evaporated to dryness. There was thus obtained as an oil 7α-(9-methylaminononyl)oestra-1,3,5(10)-triene-3,17β-diol, the structure of which was confirmed by proton magnetic resonance and mass spectroscopy.

Aufarbeitung

  1. temperatureunder reflux for 2 hours
  2. temperaturecooled
  3. customThe tetrahydrofuran was removed by evaporation
  4. extractionextracted three times with ethyl acetate (10 ml
  5. washThe combined extracts were washed with water (2 ml.)
  6. customdried
  7. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-b92b1eca10c04c8d868dc302b01b0678
Quelldatensatz
uspto-grants-1987_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04659516

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