Methyl iodide → 6-Methoxy-10-(4-methoxy-phenyl)-7-methyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene

HRID 418938Notes

Reaction equation

HRID 418938 reaction equation
Br[C:2]1[CH:15]=[C:14]2[C:5]([CH:6]3[CH:11]([CH:12]([C:16]4[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=4)[CH2:13]2)[CH2:10][CH2:9][CH2:8][CH2:7]3)=[CH:4][C:3]=1[O:24][CH3:25].C[Li].[Li][C:29](C)(C)C.CI>>[CH3:25][O:24][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][C:2]=1[CH3:29])[CH2:13][CH:12]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)[CH:11]1[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

5

Reactant 4

HCID 6328Methyl iodideHCID 666520557-Bromo-6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthreneHCID 178418306HCID 178418306, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 666519486-Methoxy-10-(4-methoxy-phenyl)-7-methyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthreneYield 100%

Procedure

At −78° C., combine 7-Bromo-6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene (chiral) (0.027 g, 0.067 mmol), and CH3Li (0.09 ml, 1.6M), then add t-BuLi (0.1 ml, 1.7M). After 30 minutes add CH3I (0.04 ml, 0.61 mmol) and remove cooling. After 1 hour at r.t., add ammonium chloride solution solution and ethyl acetate. Wash organic layer with water, dry over anhydrous sodium sulfate, remove solvent in vacuo to yield the titled compound (0.026 g, 100%). 1H NMR (CDCl3):): 7.27 (d, J=8.8 Hz, 2H), 6.99 (s, 1H), 6.93 (d, J=8.8 HZ, 2H), 6.89 (s, 1H), 3.87 (s, 3H), 3.86 (s, 3H), 3.2 (m, 2H), 2.85 (dd, J=4 and 11, 1H), 2.48 (d, J=14 Hz, 1H), 2.06 (m, 1H), 1.8-0.8 (m, 8H).

Workup

  1. customAt −78° C.
  2. customremove
  3. temperaturecooling
  4. additionadd ammonium chloride solution solution and ethyl acetate
  5. dry with materialWash organic layer with water, dry over anhydrous sodium sulfate
  6. customremove solvent in vacuo

Sources & evidence

ORD record
ord-0f53dd8785f84771afa8cde7cf4fc60a
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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