Sodium Hydroxide → Di-tert-butyl dicarbonate

Participants

Reaction Conditions

Reaction Steps

N-BOC-bromoethylamine was prepared as follows. 2-Bromoethylamine hydrobromide (6.15 g, 30 mmol) was dissolved in a mixture of 30 mL each water and dioxane and the solution was chilled in an ice bath to 0-5° C. Separately, a solution of 3.27 g (15 mmol) di-tert-butyl-dicarbonate in 35 mL dioxane was prepared. Finally a solution of 1 N sodium hydroxide (30 mL), was prepared. Dropwise addition of the di-tert-butyl-dicarbonate and the 1 N sodium hydroxide solutions to the stirred 2-bromoethylamine hydrobromide solution was begun at 0-5° C. The di-tert-butyl-dicarbonate addition took place over 30 min, and the 1N sodium hydroxide addition was complete after 15 min.

Provenance & Evidence