Methanol → (17alpha)-17-Hydroxy-3-oxoandrosta-4,9(11)-diene-17-carbonitrile

HRID 615563

反応式

HRID 615563 の反応式
CC(C)(O)[C:3]#[N:4].[C-]#N.[K+].[CH3:10][C@:11]12[CH2:28][CH:27]=[C:26]3[C@@H:16]([CH2:17][CH2:18][C:19]4[C@:24]3([CH3:25])[CH2:23][CH2:22][C:21](=[O:29])[CH:20]=4)[C@@H:15]1[CH2:14][CH2:13][C:12]2=[O:30].CO>O>[C:3]([C@@:12]1([OH:30])[CH2:13][CH2:14][C@H:15]2[C@H:16]3[C:26](=[CH:27][CH2:28][C@:11]12[CH3:10])[C@:24]1([CH3:25])[C:19](=[CH:20][C:21](=[O:29])[CH2:22][CH2:23]1)[CH2:18][CH2:17]3)#[N:4]

参加物

6

反応物 4

HCID 887MethanolHCID 6406Acetone CyanohydrinHCID 9032Potassium CyanideHCID 2395959-Dehydroandrostenedione

生成物 1

HCID 10859900(17alpha)-17-Hydroxy-3-oxoandrosta-4,9(11)-diene-17-carbonitrile

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Acetone cyanohydrin (5 ml) and sufficient potassium cyanide to adjust the pH to 9.9 is added to a slurry of androst-4,9(11)-dien-3,17-dione (0,5 g), methanol (40 ml) and water (2.5 g) at 40°. The reaction becomes homogeneous followed by precipitation of the product. After 3.5 hours, water (7.5 ml) is added dropwise and the reaction is allowed slowly to stir at 20°-25° overnight. The slurry is cooled on in ice bath, filtered, the solids washed with methanol/water (1/1) and dried under reduced pressure to give the title compound (4.54 g); [α]D (c=1, CHCl3)=+118°; MS=311, 296 and 284 m/e; NMR (CDCl3)=0.97, 1.37, 2.9, 5.5 and 5.70 δ

後処理

  1. customThe reaction becomes homogeneous followed by precipitation of the product
  2. additionwater (7.5 ml) is added dropwise
  3. temperatureThe slurry is cooled on in ice bath
  4. filtrationfiltered
  5. washthe solids washed with methanol/water (1/1)
  6. customdried under reduced pressure

出典と根拠

ORDレコード
ord-8a0849042e164ed8a4ffcaad2463fca1
出典データセット
uspto-grants-1985_02
特許番号
US04500461

関連ノート

読み込み中…