Water → 3beta-(2-(N-(2-(1-Pyrrolidinyl)ethyl)methylamino)ethylthio)-17beta-(3-furyl)-5beta-androstan-14beta-ol

HRID 1647638Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1647638
[N:1]1([CH2:6][CH2:7][NH:8][CH3:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].S(O[CH2:23][CH2:24][S:25][C@H:26]1[CH2:43][CH2:42][C@@:41]2([CH3:44])[C@H:28]([CH2:29][CH2:30][C@@H:31]3[C@@H:40]2[CH2:39][CH2:38][C@@:36]2([CH3:37])[C@:32]3([OH:50])[CH2:33][CH2:34][C@@H:35]2[C:45]2[CH:49]=[CH:48][O:47][CH:46]=2)[CH2:27]1)(C1C=CC(C)=CC=1)(=O)=O.O>CN(C)C=O>[N:1]1([CH2:6][CH2:7][N:8]([CH3:9])[CH2:23][CH2:24][S:25][C@H:26]2[CH2:43][CH2:42][C@@:41]3([CH3:44])[C@H:28]([CH2:29][CH2:30][C@@H:31]4[C@@H:40]3[CH2:39][CH2:38][C@@:36]3([CH3:37])[C@:32]4([OH:50])[CH2:33][CH2:34][C@@H:35]3[C:45]3[CH:49]=[CH:48][O:47][CH:46]=3)[CH2:27]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 295976Methyl(2-(pyrrolidin-1-yl)ethyl)amineHCID 867487853beta-(2-Tosyioxyethylthio)-17beta-(3-furyl)-5beta-androstan-14beta-ol

Produkt 1

HCID 700460273beta-(2-(N-(2-(1-Pyrrolidinyl)ethyl)methylamino)ethylthio)-17beta-(3-furyl)-5beta-androstan-14beta-olAusbeute 60,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of 0.34 g of N-(2-(1-pyrrolidinyl)ethyl) methylamine in 5 ml of dimethylformamide, 0.045 g of NaH (60% dispersion in mineral oil) were added under nitrogen and the mixture was stirred at room temperature for half an hr; a solution of 0.50 g of 3β-(2-tosyloxyethylthio)-17β-(3-furyl)-5β-androstan-14β-ol, prepared as described in Ex. 51, in 2 ml of dimethylformamide was added, the mixture was stirred for another 4 hrs and then 7 ml of water were poured in. The residue was extracted with ethyl acetate, the organic solution was washed with water to neutral pH, dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The crude product was purified by flash-chromatography (SiO2) using methylene chloride/methanol 95/5 as eluant to give 0.28 g of the title compound (I-ca)as an amorphous solid.

Aufarbeitung

  1. stirringthe mixture was stirred for another 4 hrs
  2. extractionThe residue was extracted with ethyl acetate
  3. washthe organic solution was washed with water to neutral pH
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated to dryness under reduced pressure
  6. customThe crude product was purified by flash-chromatography (SiO2)

Quellen und Nachweise

ORD-Eintrag
ord-509622baa2334647a31641295bd5bfbd
Quelldatensatz
uspto-grants-1995_07
Patentnummer
US05432169

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