Methyl bromoacetate → N-Boc-allylglycine methyl ester

Participants

Reaction Steps

To a solution of tert-Butyl allylcarbamate (7.2 g, 46 mmol) in THF at −78° C. was added LDA (31 mL, 1.5 M in cyclohexane) by syringe. The reaction was allowed to stir for 10 minutes before methyl bromoacetate (7.0 g, 46 mmol) was added. The reaction was then allowed to warm to RT. The reaction was quenched with water, extracted with EtOAc, dried over magnesium sulfate, and purified by silica gel chromatography (with 15% EtOAc-Hexanes). Removal of solvents provided the title compound. LC-MS (IE, m/z): 130 [M−Boc+1]+.

Provenance & Evidence