Water → Tert-butyl [2-(2-cyanoethoxy)ethyl]carbamate

HRID 410983Notes

Reaction equation

HRID 410983 reaction equation
[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].C(OCC)(=O)C.O.[C:19](#[N:22])[CH:20]=[CH2:21]>>[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9][O:10][CH2:21][CH2:20][C:19]#[N:22])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 962WaterHCID 7855AcrylonitrileHCID 8857Ethyl AcetateHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamate

Product 1

HCID 85735740Tert-butyl [2-(2-cyanoethoxy)ethyl]carbamate

Conditions

Temperature
50 °C

Procedure

[2-(2-Cyano-ethoxy)-ethyl]-carbamic acid tert-butyl ester (430 mg) was prepared starting from (2-hydroxy-ethyl)-carbamic acid tert-butyl ester (320 mg) in acrylonitrile (1.5 mL). The reaction was heated to 50° C. for 1 h. The reaction was added to ethyl acetate (20 mL) and water (20 mL). The phases were separated and the aqueous phase was extracted twice with ethyl acetate. The combined organics were dried over sodium sulfate and then filtered. The solvent was evaporated and crude compound was purified by flash chromatography using hexane:ethyl actetate gradient.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted twice with ethyl acetate
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated
  6. customcrude compound was purified by flash chromatography

Sources & evidence

ORD record
ord-a94ddfcfea13446c80c4efd454500b28
Source dataset
uspto-grants-2014_06
Patent number
US08759535B2

Reaction notes

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