反应详情

温度

50 °C

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.

1. customThe flask was carefully evacuated
2. additionrefilled with H2 (3×)
3. filtrationThe black suspension was filtered through Celite
4. washThe Celite was rinsed with EtOH
5. concentrationThe filtrate was concentrated in vacuo
6. temperatureTo an ice-cooled solution of the residue in DCM (1.8 mL)
7. addition4M HCl in dioxane (2.6 mL) was added
8. stirringThe resulting solution was stirred at r.t. for 18 hours
9. concentrationThe reaction mixture was concentrated in vacuo
10. dissolutionThe residue, redissolved in DMF (2 mL)
11. customwas purified by prep
12. customHPLC (column: Atlantis, 19×30 mm, 5 um, UV/MS, acidic conditions) and evaporated