Methyl iodide → HCID 69625236, compound

HRID 49413Notes

Reaction equation

HRID 49413 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@@:19]45[CH2:32][C@@H:20]4[CH2:21][C:22](=[O:31])[C@:23]5([CH2:25][CH2:26]3)[CH3:24])[C@H:17]([CH3:33])[CH2:16][C:15]=2[CH:14]=1.I[CH3:35].[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@@:19]45[CH2:32][C@@H:20]4[C@@H:21]([CH3:35])[C:22](=[O:31])[C@:23]5([CH2:25][CH2:26]3)[CH3:24])[C@H:17]([CH3:33])[CH2:16][C:15]=2[CH:14]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 69625115(7alpha,14beta,15beta)-3-Methoxy-7-methyl-14,15-methyleneestra-1,3,5 (10)-trien-17-one

Product 1

HCID 69625236HCID 69625236, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

i)—A solution of lithium bis(trimethylsilyl)amide (20.2 mmol) in tetrahydrofuran (35 ml) was cooled to −40° C. A solution of (7α,14β,15β)-3-methoxy-7-methyl-14,15-methyleneestra-1,3,5 (10)-trien-17-one (Example 1, step ii; 5.60 g) in dry tetrahydrofuran (24 ml) was added dropwise and the reaction mixture was stirred for 30 min. Then, at −30° C., iodomethane (2.4 ml) was added and stirring was continued for 45 min. 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 brine, dried over sodium sulfate and concentrated under reduced pressure, to give (7α,14β,15β,16α)-3-methoxy-7,16-dimethyl-14,15-methyleneestra-1,3,5(10)-trien-17-one (5.99 g). The product was used in the following step without further purification.

Workup

  1. stirringstirring
  2. waitwas continued for 45 min
  3. extractionthe product was extracted into ethyl acetate
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f9779105384c406b97e6f50f7bc6b266
Source dataset
uspto-grants-2004_03
Patent number
US06706700B2

Reaction notes

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