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

HRID 1741943

반응식

HRID 1741943 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

HCID 67847883N-[(5alpha,17beta)-Androstan-17-yl]-1,6-hexanediamine수율 124.9%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-289007ba1fba41b4ba12276f2c7e73b4
출처 데이터셋
uspto-grants-1994_08
특허 번호
US05334712

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