1,2-Dimethylhydrazine → (7-alpha)-3-Methoxy-7-propylestra-1,3,5(10)-trien-17-one dimethylhydrazone

HRID 1421557

반응식

HRID 1421557 반응식
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@H:9]4[C@@:13]([CH2:15][CH2:16]3)([CH3:14])[C:12](=O)[CH2:11][CH2:10]4)[C@H:7]([CH2:22][CH2:23][CH3:24])[CH2:6][C:5]=2[CH:4]=1.C[NH:26][NH:27][CH3:28].F[C:30](F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[CH3:30][N:27]([CH3:28])[N:26]=[C:12]1[CH2:11][CH2:10][C@H:9]2[C@H:8]3[C@H:17]([CH2:16][CH2:15][C@:13]12[CH3:14])[C:18]1[CH:19]=[CH:20][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[CH2:6][C@H:7]3[CH2:22][CH2:23][CH3:24]

참가 물질

6

반응물 4

HCID 13221,2-DimethylhydrazineHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 15380114(7-alpha)-3-Methoxy-7-propylestra-1,3,5(10)-trien-17-one

생성물 1

HCID 57269376(7-alpha)-3-Methoxy-7-propylestra-1,3,5(10)-trien-17-one dimethylhydrazone

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of 11.2 g. of 7a-propyl-3-O-methylestrone 5 in 60 ml of toluene were added 6 ml of dimethylhydrazine and 0.5 ml. of trifluoroacetic acid. The mixture was refluxed for 1.5 hr. After cooling to r.t. the reaction mixture was neutralized with 5% NaHCO3 and the organic layer was washed several times with water and dried over sodium sulfate. After concentration and chromatography 11.4 g of the hydrazone 6 remained as an oil; Rf 030 (hept/ethylac. 7/3).

후처리

  1. temperatureThe mixture was refluxed for 1.5 hr
  2. washthe organic layer was washed several times with water
  3. dry with materialdried over sodium sulfate
  4. concentrationAfter concentration and chromatography 11.4 g of the hydrazone 6

출처 및 근거

ORD 기록
ord-3e54e0df0bbd4eee9818d67738ee763e
출처 데이터셋
uspto-grants-2000_06
특허 번호
US06077873

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