Methyl iodide → HCID 69283487, compound

HRID 1815779Notes

Reaction equation

HRID 1815779 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:11][O:12][C:13]1[CH:30]=[CH:29][C:28]2[C@@H:27]3[C@H:18]([C@@H:19]4[C@@:23]([CH2:25][CH2:26]3)([CH3:24])[C:22](=[O:31])[CH2:21][CH2:20]4)[C@H:17]([CH3:32])[CH2:16][C:15]=2[CH:14]=1.I[CH3:34].[Cl-].[NH4+]>O1CCCC1>[CH3:11][O:12][C:13]1[CH:30]=[CH:29][C:28]2[C@@H:27]3[C@H:18]([C@@H:19]4[C@@:23]([CH2:25][CH2:26]3)([CH3:24])[C:22](=[O:31])[C@@H:21]([CH3:34])[CH2:20]4)[C@H:17]([CH3:32])[CH2:16][C:15]=2[CH:14]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 58786252HCID 58786252, compound

Product 1

HCID 69283487HCID 69283487, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

i)—A solution of lithium bis(trimethylsilyl)amide (55.5 mmol) in tetrahydrofuran (96 ml) was cooled to 40° C. A solution of (7α,14β)-3-methoxy-7-methylestra-1,3,5(10)-trien-17-one (Example 4, step ii; 15.0 g) in dry tetrahydrofuran (66 ml) was added dropwise and the reaction mixture was stirred for 45 min. Then, at −30° C., iodomethane (6.3 ml) was added and stirring was continued for 1 h (−30<T −20° C.). The mixture was poured into a saturated aqueous solution of ammonium chloride and the product was extracted into ethyl acetate. The combined organic phases were washed with water and brine, dried over sodium sulfate and concentrated under reduced pressure, to give (7α,14β,16β)-3-methoxy-7,16-dimethylestra-1,3,5(10)-trien-17-one (17.33 g). The product was used in the following step without further purification.

Workup

  1. stirringstirring
  2. waitwas continued for 1 h
  3. custom(−30<T −20° C.)
  4. extractionthe product was extracted into ethyl acetate
  5. washThe combined organic phases were washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-030b48c8c92f4b91a0ab00ae47fa8502
Source dataset
uspto-grants-2005_04
Patent number
US06881728B1

Reaction notes

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