Sodium Bicarbonate → tert-Butyl 4-(2-(4-aminonaphthalen-1-yloxy)ethyl)pyridin-2-ylcarbamate

Participants

Reaction Steps

tert-Butyl 4-(2-(4-nitronaphthalen-1-yloxy)ethyl)pyridin-2-ylcarbamate (11) (5.20 g, 12.7 mmol) and iron mesh (4.30 g, 76 mmol) were suspended in a mixture of AcOH and EtOH (1:2, 120 mL). The suspension was placed in a pre-heated oil bath at 60° C. and stirred rapidly until the reaction was judged to be complete by LC-MS. The mixture was cooled to RT, poured carefully onto saturated aq NaHCO3 (1000 mL) and extracted with EtOAc (500 mL×2). The combined organic layers were washed with further saturated aq NaHCO3 (1000 mL), water (1000 mL), brine (1000 mL) and dried. This was filtered and evaporated to give tert-butyl 4-(2-(4-aminonaphthalen-1-yloxy)ethyl)pyridin-2-ylcarbamate (13) as a yellow oil (5.00 g, 95%): m/z 380 (M+H)+ (ES+).

Provenance & Evidence