Ethanolamine → Tert-butyl 2-[(2-hydroxyethyl)amino]acetate

HRID 54615Notes

Reaction equation

HRID 54615 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].Br[CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].C(N(CC)CC)C>CN(C)C=O>[C:10]([O:9][C:7](=[O:8])[CH2:6][NH:4][CH2:3][CH2:1][OH:2])([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 8471TriethylamineHCID 79177tert-Butyl bromoacetate

Product 1

HCID 11062917Tert-butyl 2-[(2-hydroxyethyl)amino]acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound is prepared, in analogy with Example 1, from ethanolamine (18.33 g; 0.3 mol) and tert-butyl bromoacetate 58.6 g; 0.3 mol) in the presence of triethylamine (30.7 g; 0.3 mol) in anhydrous N,N-dimethylformamide (300 ml). The crude product is purified by chromatography on silica gel (eluent: chloroform/methanol, 16:1). Yield: 33.65 g (64%).

Workup

  1. customThe crude product is purified by chromatography on silica gel (eluent: chloroform/methanol, 16:1)

Sources & evidence

ORD record
ord-0e3cdfb1f75f4415884ee63d02462007
Source dataset
uspto-grants-1997_04
Patent number
US05623049

Reaction notes

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