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

HRID 1421557Notes

Reaction equation

HRID 1421557 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-3e54e0df0bbd4eee9818d67738ee763e
Source dataset
uspto-grants-2000_06
Patent number
US06077873

Reaction notes

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