Potassium Sodium Tartrate → tert-Butyl (5-(hydroxymethyl)isoquinolin-3-yl)carbamate

Participants

Reaction Steps

A 10 mL round bottom flask with methyl 3-((tert-butoxycarbonyl)amino)isoquinoline-5-carboxylate (0.2 g, 0.662 mmol) in 6 mL THF was charged with DIBAL (3.3 mL, 3.31 mmol), The reaction mixture was stirred at rt. After stirring for 2 h, the reaction mixture was added with Rochelle's salt and stirred for 1 h and then extracted with EtOAc (3×20 mL). Combined organic layer was dried, filtered and then concentrated in vacuo. Purified by silica gel chromatography (0-100% EtOAc in hexane) yielded tert-butyl (5-(hydroxymethyl)isoquinolin-3-yl)carbamate (26-4).

Provenance & Evidence