Methyl iodide → 2-[[N-(tert-butyloxycarbonyl)-N-methylamino]methyl]pyridine

HRID 1603810Notes

Reaction equation

HRID 1603810 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:18]I>O1CCCC1>[C:1]([O:5][C:6]([N:8]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[CH3:18])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12069550N-Boc-2-aminomethylpyridine

Product 1

HCID 196062132-[[N-(tert-butyloxycarbonyl)-N-methylamino]methyl]pyridineYield 70.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 19.8 g (95 mmol) of 2-(N-(t-butyloxycarbonyl)aminomethyl)-pyridine in anhydrous tetrahydrofuran was cooled under N2 atmosphere to 0° C. and treated with 4.95 g (124 mmol) of sodium hydride (60% dispersion in oil). The solution was stirred for 15 min, treated dropwise with 7.1 ml (114 mmol) of methyl iodide, stirred at ambient temperature for 2 h, and quenched cautiously with water. The resulting mixture was partitioned between ether and water, dried over Na2SO4, and concentrated in vacuo. Chromatography on silica gel provided 14.9 g (70%) of the desired compound as a colorless oil. 1H NMR (CDCl3) δ 1.43, 1.49 (two s, 9 H), 2.89, 2.94 (two s, 3 H), 4.54, 4.57 (two s, 2 H), 7.2 (m, 2 H), 7.67 (td, J=8, 2 Hz, 1 H), 8.55 (d, J=4 Hz, 1 H). Mass spectrum: (M+H)+ =223.

Workup

  1. stirringstirred at ambient temperature for 2 h
  2. customquenched cautiously with water
  3. customThe resulting mixture was partitioned between ether and water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-31299486231840ca8945d5575460f80d
Source dataset
uspto-grants-1999_11
Patent number
US05990135

Reaction notes

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