Methyl iodide → HCID 18374763, compound

HRID 2301191Notes

Reaction equation

HRID 2301191 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:28]I>O1CCCC1.C(OCC)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:12][CH:13]2[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]2)[CH3:28])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18374698HCID 18374698, compound

Product 1

HCID 18374763HCID 18374763, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(N-((4-Fluorophenyl)sulfonyl)aminomethyl)-1-tert-butoxycarbonylpiperidine (100 mg, 0.27 mmol, from Example 87, Step A) was added to a slurry of sodium hydride (12 mg, 60% in mineral oil, 0.30 mmol) in 5 mL of dry tetrahydrofuran at 0° C. under nitrogen. Methyl iodide (0.022 mL, 0.35 mmol) was then added. The reaction mixture was then allowed to warm to room temperature overnight. The mixture was diluted with diethyl ether and washed with 1N NaOH and brine. The solution was dried over Na2SO4, filtered and concentrated to provide 98 mg (94% yield) of the title compound. ESI−MS. M/z; (M+H)=387.0.

Workup

  1. washwashed with 1N NaOH and brine
  2. dry with materialThe solution was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4b882f576f254948a7f6b95b8118cfde
Source dataset
uspto-grants-2002_12
Patent number
US06498161B1

Reaction notes

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