Acetic Acid → 17-Cyano-9,17-dihydroxyandrost-4-ene-3-one

HRID 1650075ノート

反応式

HRID 1650075 の反応式
C(O)(=[O:3])C.O[C@H:6]1[CH2:23][C@@:21]2([CH3:22])[C@@H:17]([CH2:18][CH2:19][C:20]2=O)[C@H:16]2[C@H:7]1[C@:8]1([CH3:27])[C:13]([C@@H:14](C)[CH2:15]2)=[CH:12]C(=O)[CH:10]=[CH:9]1.[C-:28]#[N:29].[K+].[OH2:31].[CH3:32][OH:33]>>[CH3:22][C@@:21]12[C:20]([OH:31])([C:28]#[N:29])[CH2:19][CH2:18][C@H:17]1[C@@H:16]1[CH2:15][CH2:14][C:13]3[C@@:8]([CH3:27])([C:7]1([OH:3])[CH2:6][CH2:23]2)[CH2:9][CH2:10][C:32](=[O:33])[CH:12]=3

参加物

6

反応物 5

HCID 176Acetic Acid3 回HCID 887MethanolHCID 962Water2 回HCID 9032Potassium CyanideHCID 1508605911beta-Hydroxy-6alpha-methylandrosta-1,4-diene-3,17-dione

生成物 1

HCID 308277817-Cyano-9,17-dihydroxyandrost-4-ene-3-one

実験手順

Glacial acetic acid (2.87 ml) is added to 9α-hydroxyandrost-4-ene-3,17-dione (0, 13.49 g) and potassium cyanide (4.98 g) slurried in methanol (45 ml) and stirred at 20°-25°. Glacial acetic acid (0.92 ml) is added followed by water (30 ml) over 13.7 hr via a syringe pump, keeping the mixture at 27°. The mixture is stirred an additional 2 hr at 27°. Additional glacial acetic acid (1.5 ml) is added at 15° followed by water (50 ml) at 10°. The mixture is stirred at 10° for 20 min and the product collected by vacuum filtration and washed with water. The solid is dried in an air stream for 24 hr to give the title compound, mp 229°-230°.

後処理

  1. customat 27°
  2. stirringThe mixture is stirred an additional 2 hr at 27°
  3. stirringThe mixture is stirred at 10° for 20 min
  4. filtrationthe product collected by vacuum filtration
  5. washwashed with water
  6. customThe solid is dried in an air stream for 24 hr

出典と根拠

ORDレコード
ord-2fe352cd6628469e907ec94216c895ac
出典データセット
uspto-grants-1990_05
特許番号
US04921638

反応ノート

読み込み中…