p-Toluenesulfonic acid → (8S,10R,13S,14S)-3-methoxy-10,13-dimethyl-1,2,7,8,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-one

HRID 247539

反応式

HRID 247539 の反応式
[CH3:1][C@:2]12[CH2:19][CH:18]=[C:17]3[C@@H:7]([CH2:8][CH2:9][C:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C:12](=[O:20])[CH:11]=4)[C@@H:6]1[CH2:5][CH2:4][C:3]2=[O:21].O1CCOC[CH2:23]1.COC(OC)OC.C1(C)C=CC(S(O)(=O)=O)=CC=1>N1C=CC=CC=1>[CH3:23][O:20][C:12]1[CH2:13][CH2:14][C@@:15]2([CH3:16])[C:10](=[CH:9][CH2:8][C@@H:7]3[C:17]2=[CH:18][CH2:19][C@@:2]2([CH3:1])[C@H:6]3[CH2:5][CH2:4][C:3]2=[O:21])[CH:11]=1

参加物

6

反応物 4

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 312751,4-DioxaneHCID 2395959-Dehydroandrostenedione

生成物 1

HCID 13037635(8S,10R,13S,14S)-3-methoxy-10,13-dimethyl-1,2,7,8,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-one

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

11.5 g of 4,9(11)-androstadiene-3,17-dione [U.S. Pat. No. 3,441,559 (1969)]in 200 ml of dioxane is reacted with 20 ml of orthoformic acid trimethyl ester and 100 mg of p-toluenesulfonic acid. After 48 hours, 5 ml of pyridine is added to the solution, the latter is concentrated under vacuum, the residue taken up in ethyl acetate, washed with water, and dried over sodium sulfate. After chromatography of the crude product with a hexane-ethyl acetate gradient on silica gel containing 2% triethylamine, 9.2 g of 3-methoxy-3,5,9(11)-androstatrien-17-one is isolated; mp 153.4° C.

後処理

  1. concentrationthe latter is concentrated under vacuum
  2. washwashed with water
  3. dry with materialdried over sodium sulfate

出典と根拠

ORDレコード
ord-9e421d8e61ef44e9b5e5876a0ec3ea0b
出典データセット
uspto-grants-1987_11
特許番号
US04708823

関連ノート

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