Acetic Acid → 3beta-[N-(2-AMINOETHYL)-AMINO]-17beta-HYDROXY-5alpha-ANDROSTANE

HRID 375673

反応式

HRID 375673 の反応式
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C@H:11]([CH2:12][C:13](=O)[CH2:14][CH2:15]1)[CH2:10][CH2:9]3.[CH2:22]([NH2:25])[CH2:23][NH2:24].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[NH2:24][CH2:23][CH2:22][NH:25][C@H:13]1[CH2:14][CH2:15][C@@:16]2([CH3:17])[C@@H:11]([CH2:10][CH2:9][C@@H:8]3[C@@H:18]2[CH2:19][CH2:20][C@@:3]2([CH3:4])[C@H:5]3[CH2:6][CH2:7][C@@H:2]2[OH:1])[CH2:12]1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 3301EthylenediamineHCID 10635DihydrotestosteroneHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 153088353beta-[N-(2-AMINOETHYL)-AMINO]-17beta-HYDROXY-5alpha-ANDROSTANE

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

17β-Hydroxy-5α-androstan-3-one (403 mg, 1.39 mmol)(Aldrich Chemical Company) was added to a stirred solution of 0.745 mL 1,2-ethylenediamine (11.1 mmol) and 1.44 mL acetic acid (25.2 mmol) in 16.0 mL dry methanol (MeOH), followed by 104 mg (1.65 mmol, 1.19 equiv.) of sodium cyanoborohydride. After stirring at room temperature for 15 h, the reaction concentrated under reduced pressure. The residue was partitioned between methylene chloride and aqueous 1N sodium hydroxide, shaken, and separated. The organic layer was washed with water, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The product was used without further purification.

後処理

  1. concentrationthe reaction concentrated under reduced pressure
  2. customThe residue was partitioned between methylene chloride and aqueous 1N sodium hydroxide
  3. stirringshaken
  4. customseparated
  5. washThe organic layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe product was used without further purification

出典と根拠

ORDレコード
ord-1c2136c9e3014b3da2cb9b7402937b62
出典データセット
uspto-grants-1996_01
特許番号
US05486603

関連ノート

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