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

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

Reactant 4

HCID 962Water

HCID 7855Acrylonitrile

HCID 8857Ethyl Acetate

HCID 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.