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

HRID 464577

반응식

HRID 464577 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-37900ee7da7e41ea8e3f34a00ee285af
출처 데이터셋
uspto-grants-1985_10
특허 번호
US04548748

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