Androstenedione → (17alpha)-17-Hydroxy-3-oxoandrost-4-ene-17-carbonitrile

HRID 464576

反応式

HRID 464576 の反応式
CC(C)(O)[C:3]#[N:4].[C-]#N.[K+].[CH3:10][C@:11]12[CH2:28][CH2:27][C@H: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@H:26]([CH2:27][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 3

HCID 6128AndrostenedioneHCID 6406Acetone CyanohydrinHCID 9032Potassium Cyanide

生成物 1

HCID 13035453(17alpha)-17-Hydroxy-3-oxoandrost-4-ene-17-carbonitrile

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒3 回

実験手順

Acetone cyanohydrin (82 ml), potassium cyanide (1 gm) and water (2 ml) are added to a slurry of androst-4-en-3,17-dione (0.80 g) in methanol (400 ml) and water (40 ml) at 35°. The reaction becomes homogeneous and on continued stirring a heavy slurry develops. After 3 hours, 120 ml of water is added dropwise, and the slurry allowed to stir overnight at 20°-25°. The slurry is then cooled in an ice bath, filtered, and the solids washed with methanol/water (1/1). The solvents are dried under reduced pressure to give 70.4 g of the title compound. An additional 13.17 g of product is isolated from the mother liquor on partial evaporation, m.p.=159°-160.5°; [α]D (c=1, CHCl3)=+145.9°; MS=313, 298, 286, 245 and 124 m/e; NMR (CDCl3)=1.00, 1.20, 3.5 and 5.72 δ

後処理

  1. stirringto stir overnight at 20°-25°
  2. temperatureThe slurry is then cooled in an ice bath
  3. filtrationfiltered
  4. washthe solids washed with methanol/water (1/1)
  5. customThe solvents are dried under reduced pressure

出典と根拠

ORDレコード
ord-6607ed1595b046a1ad703fe90d4a9fa8
出典データセット
uspto-grants-1985_10
特許番号
US04548748

関連ノート

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