Sodium Hydroxide → N-[(5alpha,17beta)-Androstan-17-yl]-1,6-hexanediamine

HRID 1614480

Reaktionsgleichung

Reaktionsgleichung von HRID 1614480
[CH2:1]([NH2:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].[CH3:9][C@:10]12[CH2:27][CH2:26][C@H:25]3[C@@H:15]([CH2:16][CH2:17][C@@H:18]4[C@:23]3([CH3:24])[CH2:22][CH2:21][CH2:20][CH2:19]4)[C@@H:14]1[CH2:13][CH2:12][C:11]2=O.C([BH3-])#N.[Na+].[OH-].[Na+]>O1CCCC1.C(O)(=O)C.CO>[CH3:9][C@:10]12[CH2:27][CH2:26][C@H:25]3[C@@H:15]([CH2:16][CH2:17][C@@H:18]4[C@:23]3([CH3:24])[CH2:22][CH2:21][CH2:20][CH2:19]4)[C@@H:14]1[CH2:13][CH2:12][C@@H:11]2[NH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][NH2:8]

Komponenten

8

Edukt 4

HCID 14798Sodium HydroxideHCID 16402HexamethylenediamineHCID 1019275alpha-Androstan-17-oneHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 67847883N-[(5alpha,17beta)-Androstan-17-yl]-1,6-hexanediamineAusbeute 124,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A 100 ml round-bottomed flask, equipped with a magnetic stir bar, condenser, and nitrogen inlet tube, was charged with 1,6-hexanediamine (0.904 g) and 15 ml of methanol. The solution was treated with glacial acetic acid until the pH was 6.7. To this mixture was added 15 ml of tetrahydrofuran, 5α-androstan-17-one (0.704 g) and sodium cyanoborohydride (0.228 g). The mixture was heated to reflux for 18 h. After cooling, the solution was made basic with aqueous 2M sodium hydroxide to a pH of 13-14. The solution was extracted with chloroform (3×) and the combined organic layers were washed with water and brine, dried (Na2SO4), filtered, and concentrated to give 1.2 g of an oil.

Aufarbeitung

  1. customA 100 ml round-bottomed flask, equipped with a magnetic stir bar, condenser, and nitrogen inlet tube
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 18 h
  4. temperatureAfter cooling
  5. extractionThe solution was extracted with chloroform (3×)
  6. washthe combined organic layers were washed with water and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-789156abb9c240ff9950dea785b16ca3
Quelldatensatz
uspto-grants-1993_03
Patentnummer
US05196542

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