Methyl iodide → HCID 19974930, compound

HRID 1451523Notes

Reaction equation

HRID 1451523 reaction equation
[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH2:18][CH:19]([CH3:24])[C:20]([O:22][CH3:23])=[O:21])=[C:8]2[CH3:25])=[CH:4][CH:3]=1.[Li+].[CH3:29]C([N-]C(C)C)C.IC>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C>[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH2:18][C:19]([CH3:29])([CH3:24])[C:20]([O:22][CH3:23])=[O:21])=[C:8]2[CH3:25])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 19974940HCID 19974940, compound

Product 1

HCID 19974930HCID 19974930, compoundYield 67.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
0 °C

Procedure

To a -78° C. solution of the ester from Step 1 (35 mg, 0.08 mmol) in 3 mL THF was added LDA (1.5M in cyclohexane, 0.1 mL, 0.15 mmol), and the solution was stirred for 30 min. A solution of iodomethane (0.1 mL, 1.6 mmol) in 1 mL HMPA was then added by syringe. The solution was stirred 15 min at -78° C., then warmed to 0° C. and quenched with saturated NH4Cl. The mixture was partitioned between ether and water and the organic layer was washed with water and brine and dried over MgSO4. The residue was purified by flash chromatography (15% ethyl acetate/hexanes) to provide 24 mg of the title compound.

Workup

  1. stirringThe solution was stirred 15 min at -78° C.
  2. customquenched with saturated NH4Cl
  3. customThe mixture was partitioned between ether and water
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried over MgSO4
  6. customThe residue was purified by flash chromatography (15% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-6d84c1163068405bbbf7679acc31daea
Source dataset
uspto-grants-1997_02
Patent number
US05604253

Reaction notes

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