Methyl iodide → HCID 54538723, compound

HRID 617323Notes

Reaction equation

HRID 617323 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[CH:5]([CH2:8][OH:9])[CH2:4][C@H:3]1[CH2:10][O:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1.[H-].[Na+].[CH3:20]I>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:20][O:9][CH2:8][CH:5]1[C:6](=[O:7])[N:2]([CH3:1])[C@H:3]([CH2:10][O:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH2:4]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21309676HCID 21309676, compound

Product 1

HCID 54538723HCID 54538723, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A 327 mg (139 mmol) sample of 3-(1-methyl-4-hydroxymethyl-5-oxo-2(S)-pyrrolidinylmethoxy)pyridine, prepared as in Example 48a above, was dissolved in 13 mL of anhydrous THF, 111 mg (2.77 mmol) of NaH was added, and the mixture was stirred for 30 minutes at room temperature. To this solution was added 258 mL (4.17 mmol) of methyl iodide and 256 mg of tetrabutylammonium iodide, and the reaction was stirred at room temperature for 2 hours. The reaction was quenched by the addition of water, and the mixture was extracted with chloroform. The extract was dried over MgSO4, filtered and concentrated. The solvent was removed, and the residue was purified by column chromatography on silica gel, eluting with 10:1 chloroform:methanol to give 314 mg of the title compound. MS (DCI/NH3) m/e: 251 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 8.37-8.25 (m, 2H), 7.35-7.25 (m, 2H), 4.18-4.0 (m, 2H), 3.99-3.84 (m, 1H), 3.73-3.58 (m, 2H), 3.37 (s, 2H), 3.36 (s, 1H), 3.05 (s, 1H), 2.95 (s, 1H), 2.94 (s, 1H), 2.90-2.63 (m, 1H), 2.49-2.24 (m, 2H).

Workup

  1. stirringthe reaction was stirred at room temperature for 2 hours
  2. customThe reaction was quenched by the addition of water
  3. extractionthe mixture was extracted with chloroform
  4. dry with materialThe extract was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe solvent was removed
  8. customthe residue was purified by column chromatography on silica gel
  9. washeluting with 10:1 chloroform

Sources & evidence

ORD record
ord-2d9b709a532a4ff38ac0faee478fa5f6
Source dataset
uspto-grants-1999_09
Patent number
US05948793

Reaction notes

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