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 1032029

반응식

HRID 1032029 반응식
[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

참가 물질

6

반응물 4

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

생성물 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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-8f7441fe1ee14c1497a8aab338e52dc6
출처 데이터셋
uspto-grants-1990_09
특허 번호
US04956482

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