Ethanolamine → tert-butyl N-(2-hydroxyethyl)carbamate

HRID 1454354Notes

Reaction equation

HRID 1454354 reaction equation
[NH2:1][CH2:2][CH2:3][OH:4].[OH-].[Na+].[C:7](N=[N+]=[N-])([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]>O.O1CCOCC1>[C:7]([NH:1][CH2:2][CH2:3][OH:4])([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 14798Sodium HydroxideHCID 61256Carbonazidic acid, 1,1-dimethylethyl ester

Product 1

HCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateYield 41.1%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a cooled, stirred solution of 2-aminoethanol (5.9 ml, 0.098 mol) and sodium hydroxide (3.6 g, 0.098 mol) in water-dioxane (1:1), was added drop-wise Boc-azide (10 ml, 0.081 mol). The reaction was stirred at room temperature overnight. The dioxane was then removed under vacuum, and the water layer extracted several times with ethyl acetate. The organic layer was dried over sodium sulphate and then, evaporated to dryness under vacuum to get the product (N-Boc)-2-aminoethanol (5.37 g, 41% yield), which was used in further steps without purification.

Workup

  1. customThe dioxane was then removed under vacuum
  2. extractionthe water layer extracted several times with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. customevaporated to dryness under vacuum

Sources & evidence

ORD record
ord-7019541581f347eca10ba393a3c95cff
Source dataset
uspto-grants-2009_01
Patent number
US07479536B1

Reaction notes

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