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

HRID 1741943

反応式

HRID 1741943 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-289007ba1fba41b4ba12276f2c7e73b4
出典データセット
uspto-grants-1994_08
特許番号
US05334712

関連ノート

読み込み中…