proline dl-form → HCID 68897457, compound

Participants

Reaction Steps

3-(7-chloro-2-oxidoisoquinolin-4-yl)propanal (6-1)(300 mg, 1.27 mmol, 1.0 equiv) and N-fluorobenzenesulfonimide (442 mg, 1.40 mmol, 1.1 equiv) were dissolved in THF (11.6 mL) and isopropyl alcohol (1.16 mL). To this mixture, was added DL-proline (29.3 mg, 0.26 mmol, 0.2 equiv). The reaction mixture was stirred at room temperature overnight. LCMS showed product. To this reaction mixture, were added allylamine (191 μl, 2.55 mmol, 2.0 equiv) and sodium triacetoxyborohydride (1.08 g, 5.09 mmol, 4.0 equiv). The reaction mixture was stirred at room temperature for 3 hours before (Boc)2O (833 mg, 3.82 mmol, 3 equiv) was added. The resulted reaction mixture was stirred at room temperature overnight. The reaction mixture was then quenched with H2O, and extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated. The crude was purified with silica gel chromatography (EtOAc/Hexane=0->100%) to afford the product (6-2). LRMS m/z (M+H) 395.1 found, 395.2 required.

Provenance & Evidence