(+/-)-1-(5-chloro-2-ethoxycarbonylmethoxy-phenyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester → (+/-)-[4-Chloro-2-(1,2,3,4-tetrahydro-isoquinolin-1-yl)-phenoxy]-acetic acid ethyl ester

Participants

Reaction Steps

To a solution of (±)-1-(5-chloro-2-ethoxycarbonylmethoxy-phenyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester (1.03 g, 2.15 mmol, 1.0 eq.) in AcOH (30 mL), 33% hydrobromic acid in acetic acid (7.5 mL) was added. The mixture was stirred at r.t. for 1 hour. The reaction mixture was concentrated in vacuo. The residue was purified by flash master (column: 100 g, flow: 45 mL/min, Heptane to AcOEt with 10% of NEt3) to yield the title amine.

Provenance & Evidence