Water → HCID 131055384, compound

HRID 50619Notes

Reaction equation

HRID 50619 reaction equation
[C:1]([N:8]([CH:10](O)[CH2:11][CH2:12][CH3:13])[CH3:9])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H-].[Na+].CI.O.[O:20]1CCC[CH2:21]1>>[C:1]([N:8]([CH3:9])[CH2:10][CH2:11][CH2:12][CH2:13][O:20][CH3:21])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 5

HCID 962WaterHCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 86759403N-Boc-N-methyl amino butanol

Product 1

HCID 131055384HCID 131055384, compound

Procedure

The resulting N-Boc-N-methyl amino butanol (4.00 g) was placed in a 200-mL threeneck flask, and after nitrogen substitution, the compound was dissolved in 35 mL of anhydrous tetrahydrofuran. The solution was added with 60% sodium hydride (1.77 g), and stirred at room temperature for 30 minutes. Then, the reaction mixture was added dropwise with 1.87 mL of methyl iodide and stirred on an oil bath at 50° C. for 1.5 hours. The reaction was stopped with water, and the organic layer was extracted with ethyl acetate, washed once with water and once with saturated brine, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/4) to obtain 4.25 g of N-Boc-N-methyl-N-methoxybutylamine.

Workup

  1. stirringstirred on an oil bath at 50° C. for 1.5 hours
  2. extractionthe organic layer was extracted with ethyl acetate
  3. washwashed once with water and once with saturated brine
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/4)

Sources & evidence

ORD record
ord-853bae317a1846ed85c68f0ebc01ad71
Source dataset
uspto-grants-2004_03
Patent number
US06713473B1

Reaction notes

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