Hydrochloric Acid → HCID 86591279, compound

HRID 1369375Notes

Reaction equation

HRID 1369375 reaction equation
[CH3:1][O:2][C:3]1([O:23][CH3:24])[CH2:20][CH2:19][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]([CH3:22])[CH2:6][C:5]=2[CH2:4]1.[O:25]([NH2:27])[CH3:26].Cl.C([O-])(=O)C.[Na+].C(=O)([O-])O.[Na+]>CO.O>[CH3:26][O:25][N:27]=[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[CH2:19][CH2:20][C:3]([O:23][CH3:24])([O:2][CH3:1])[CH2:4][C:5]=1[CH2:6][C@H:7]3[CH3:22]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 4113O-MethylhydroxylamineHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 15380148(7R,8R,9S,13S,14S)-3,3-dimethoxy-7,13-dimethyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one

Product 1

HCID 86591279HCID 86591279, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

(7α)-3,3-Dimethoxy-7-methylestr-5(10)-en-17-one (100 mg, 0.3 mmol) was added to a solution of methoxylamine.HCl (100 mg, 1.2 mmol) and sodium acetate (123 mg, 1.5 mmol) in 6 mL MeOH. The reaction mixture was stirred for 3 days at room temperature. Water and a solution of saturated sodium hydrogen carbonate was added and extracted with ethyl acetate. The organic layer was washed with brine, dried (Na2SO4) and evaporated to dryness to give the crude (7α)-3,3-dimethoxy-7-methylestr-5(10)-en-17-one O-methyloxime, which was converted into (7α)-3-methylene-7-methylestr-5(10)-en-17-one O-methyloxime according to the methods described above, [α]D +149° (c 0.11 in ethanol).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-0b985c4961754214a6230b067d2db1c3
Source dataset
uspto-grants-2003_06
Patent number
US06579864B1

Reaction notes

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