Methyl iodide → HCID 15884726, compound

HRID 379515Notes

Reaction equation

HRID 379515 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH3:15])[N:4]1[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].[CH3:26]I.[H-].[Na+]>CN(C=O)C>[CH3:26][O:1][CH2:2][CH:3]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH3:15])[N:4]1[C:16]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:17]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15884725HCID 15884725, compound

Product 1

HCID 15884726HCID 15884726, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-hydroxymethyl-5-(2-methoxyphenyl)-N-(carbobenzyloxy)-tetrahydropyrrole (2.49 g, 7.30 mmol) in DMF (20 mL) at 0-40° C. was added methyl iodide (4.55 mL, 73 mmol) and NaH (60% oil dispersion, 1.75 g, 43.8 mmol) and the resulting suspension was stirred at room temperature for 1 hour. The reaction mixture was quenched with H2O at 0° C., ether was added, and the aqueous layer was extracted with ether (×4), and the combined organic layers were washed with brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The crude product was purified by silica gel flash chromatography (5% EtOAc-95% hexanes) to provide the title compound as a colorless oil. 1H NMR (CDCl3, 400 MHz) δ: 3.77 (3H, s, OMe), 3.38 (3H, s, OMe).

Workup

  1. customThe reaction mixture was quenched with H2O at 0° C.
  2. additionether was added
  3. extractionthe aqueous layer was extracted with ether (×4)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by silica gel flash chromatography (5% EtOAc-95% hexanes)

Sources & evidence

ORD record
ord-1e9638787bff4192b2706da2e0d6d58a
Source dataset
uspto-grants-2001_10
Patent number
US06300316B1

Reaction notes

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