2-(Methylamino)ethanol → N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanol

HRID 1755129Notes

Reaction equation

HRID 1755129 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].[C:6]([O:13]C([O-])=O)([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=O>C(Cl)Cl>[CH3:12][C:9]([O:8][C:6](=[O:13])[N:2]([CH2:3][CH2:4][OH:5])[CH3:1])([CH3:10])[CH3:11]

Participants

4

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 22064466Tert-butyldicarbonate

Product 1

HCID 545700N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanolYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-(methylamino)ethanol (5.2 g, 69.2 mmol) and tert-butyl dicarbonate (15.8 g, 72.7 mmol) in methylene chloride (200 mL) was stirred at room temperature for 16 hours. The reaction mixture was diluted with methylene chloride, and the organic layer was then washed with water, dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give (2-hydroxyethyl)methylcarbamic acid 1,1-dimethylethyl ester (12.1 g, yield 100%).

Workup

  1. washthe organic layer was then washed with water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bd31ce806daa4c77ba6c4dd8ea5c942c
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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