Methyl iodide → HCID 22101278, compound

HRID 727421Notes

Reaction equation

HRID 727421 reaction equation
[OH:1][CH:2]1[C:13]2=[C:14]3[C:9](=[CH:10][CH:11]=[CH:12]2)[CH:8]=[CH:7][CH:6]=[C:5]3[CH2:4][CH:3]1[NH:15][C:16](=[O:18])[CH3:17].[H-].[Na+].[CH3:21]I>CN(C=O)C>[CH3:21][O:1][CH:2]1[C:13]2=[C:14]3[C:9](=[CH:10][CH:11]=[CH:12]2)[CH:8]=[CH:7][CH:6]=[C:5]3[CH2:4][CH:3]1[NH:15][C:16](=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22101282HCID 22101282, compound

Product 1

HCID 22101278HCID 22101278, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The N-(1-hydroxy-2,3-dihydro-1H-phenalen-2-yl)acetamide obtained is stage C of Example 1 (1 mmol, 290 mg) is dissolved in 10 cm3 of anhydrous DMF. Under an inert atmosphere, NaH (1 mmol, 0.05 g of 60% in oil suspension) and then methyl iodide (0.09 cm3, 1.2 eq) are added in the reaction mixture. Stirring is maintained at ambiant temperature for 4h30 and the solvent is evaporated. The residue is taken up in CH2 Cl2 and the solution is flitrated. The filtrate is evaporated and purified by chromatography on silica gel (particle size 60-200 μm); eluent: CH2Cl2 : MeOH 99 :-1 v/v. The title product is isolated. This is and amorphous product, which is a diastereoisomer mixture.

Workup

  1. temperatureis maintained at ambiant temperature for 4h30
  2. customthe solvent is evaporated
  3. customThe filtrate is evaporated
  4. custompurified by chromatography on silica gel (particle size 60-200 μm)

Sources & evidence

ORD record
ord-20d9a9900ddb48ff9621b67c97711d5f
Source dataset
uspto-grants-1998_01
Patent number
US05712312

Reaction notes

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