tert-Butyl bromoacetate → HCID 15908942, compound

Participants

Reaction Steps

5.91 ml of tert-butyl bromoacetate is added dropwise within 30 minutes to a mixture of 15.00 g of (S)-(+)-1-amino-2-propanol and 6.97 ml of diisopropylethylamine in 100 ml of N,N-dimethylformamide, while cooling with an ice bath. Then the cooling bath is removed and the reaction mixture is stirred overnight at ambient temperature. For working up, the solvent is distilled off in vacuo, the flask residue is dissolved in 50 ml water and saturated with 15 g of sodium chloride. The aqueous phase is extracted several times with ethyl acetate. The extracts are combined, washed with 20 ml of saturated sodium chloride solution, dried over magnesium sulfate, and concentrated by evaporation. The oily yellowish crude product is reacted further without any more purification. Yield: 7.80 g (103% of theory); Rf value: 0.42 (silica gel, methylene chloride/methanol=9:1); mass spectrum (ESI+): m/z=190 [M+H]+.

Provenance & Evidence