Water → t-Butyl 2-(4-(aminomethyl)-2-bromophenoxy)acetate

Participants

Reaction Steps

t-Butyl 2-(2-bromo-4-formylphenoxy)acetate (1) (0.5 g, 1.59 mmol, 1 eq) was dissolved in MeOH (23 mL) along with HOAc (14 mL) and NH4OAc (6.23 g, 81 mmol; 51 eq). After stirring at room temperature room temperature for 4 h, sodium cyanoborohydride (146 mg; 2.27 mmol, 1.4 eq) was added and the mixture was stirred for an additional 18 h at room temperature. Water (4 mL) was added and the mixture was concentrated in vacuo. The resultant residue was purified by preparative HPLC to afford 91 mg (18.2%) of t-butyl 2-(4-(aminomethyl)-2-bromophenoxy)acetate (6).

Provenance & Evidence