Methyl iodide → HCID 18914180, compound

HRID 1292360Notes

Reaction equation

HRID 1292360 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[CH2:10][CH:9]1[CH2:21][CH2:22][OH:23])=[O:7])([CH3:4])([CH3:3])[CH3:2].I[CH3:25].[H-].[Na+]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[CH2:10][CH:9]1[CH2:21][CH2:22][O:23][CH3:25])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18914165HCID 18914165, compound

Product 1

HCID 18914180HCID 18914180, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred, 0° C. solution of 1-t-butyloxycarbonyl-2-(2-hydroxyethyl)-4-(2-methylphenyl)piperazine from Step 1 above (0.38 g; 1.2 mmol) and iodomethane (0.20 mL; 3.4 mmol) in dry THF (20 mL) was added NaH (60 mg of a 60% suspension in mineral oil; 1.5 mmol). The reaction was stirred at 0° C. for 15 min and then at ambient temperature for 18 h. The reaction was quenched by adding several drops of MeOH and the solvents were evaporated under reduced pressure. The residue was partitioned between EtOAc and water. The organic phase was separated and washed with water and brine. The organic phase was dried (MgSO4), filtered, and the solvent was removed under reduced pressure. The residue was purified by pressurized silica gel column chromatography using 1:4 EtOAc:hexanes as eluant. The title compound was obtained as a gum (1H-NMR: consistent with structure; TLC: silica gel, 1:3 EtOAc:hexanes: single component, Rf =0.62; FABMS: M+H @ m/e=335; HPLC: >99%, retention time 11.7 min).

Workup

  1. waitat ambient temperature for 18 h
  2. customThe reaction was quenched
  3. additionby adding several drops of MeOH
  4. customthe solvents were evaporated under reduced pressure
  5. customThe residue was partitioned between EtOAc and water
  6. customThe organic phase was separated
  7. washwashed with water and brine
  8. dry with materialThe organic phase was dried (MgSO4)
  9. filtrationfiltered
  10. customthe solvent was removed under reduced pressure
  11. customThe residue was purified by pressurized silica gel column chromatography

Sources & evidence

ORD record
ord-fb4b8b2d91974d36b7a4b87a6164cbe0
Source dataset
uspto-grants-1998_05
Patent number
US05756504

Reaction notes

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