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

Participants

Reaction Conditions

Reaction Steps

To a solution of (±)-1-(5-chloro-2-ethoxycarbonylmethoxy-phenyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (446 mg, 1.0 mmol, 1.0 eq.) in EtOH (4.8 mL) under N2, palladium on activated carbon (10 wt. %, 106 mg) was added. The flask was carefully evacuated and refilled with H2 (3×). The black suspension was stirred at 50° C. under an H2-atmosphere for 48 hours. The black suspension was filtered through Celite. The Celite was rinsed with EtOH. The filtrate was concentrated in vacuo. To an ice-cooled solution of the residue in DCM (1.8 mL), 4M HCl in dioxane (2.6 mL) was added. The resulting solution was stirred at r.t. for 18 hours. The reaction mixture was concentrated in vacuo. The residue was coevaporated with EtOH (3×). The residue, redissolved in DMF (2 mL), was purified by prep. HPLC (column: Atlantis, 19×30 mm, 5 um, UV/MS, acidic conditions) and evaporated to give the desired amine as a yellow oil.

Provenance & Evidence