Dihydrotestosterone → 3beta-Amino-17beta-hydroxy-5alpha-androstane

HRID 375671

反応式

HRID 375671 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.C([O-])(=O)C.[NH4+].C([BH3-])#[N:28].[Na+]>CO>[NH2:28][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

5

反応物 3

HCID 10635DihydrotestosteroneHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 146048433beta-Amino-17beta-hydroxy-5alpha-androstane

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

3β-Amino-17β-hydroxy-5α-androstane was prepared by the procedure of Boutigue et al. (1973, Bull. Soc. Chim. France 750-753). 17β-Hydroxy-5α-androstan-3-one (403 mg, 1.39 mmol) (Aldrich Chemical Company) was added to 862 mg of ammonium acetate (11.2 mmol, 8.06 equiv.) 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 was concentrated under reduced pressure. The residue was partitioned between methylene chloride and aqueous 1N sodium hydroxide (NaOH), 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 was concentrated under reduced pressure
  2. customThe residue was partitioned between methylene chloride and aqueous 1N sodium hydroxide (NaOH)
  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-2c69af2d6d98497e8dfa90838e952f9f
出典データセット
uspto-grants-1996_01
特許番号
US05486603

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