1-Methylpiperazine → t-Butyl (1R)-1-(4-(2-methylpentyloxy)phenyl)-2-(4-methylpiperazin-1-yl)ethylcarbamate

Participants

Reaction Steps

To a solution of t-butyl (1R)-1-(4-(2-methylpentyloxy)phenyl)-2-oxoethylcarbamate (80 mg, 0.238 mmol) in dichloroethane (1 mL) was added 1-methylpiperazine (0.032 mL, 0.286 mmol) followed by sodium triacetoxyborohydride (70.8 mg, 0.334 mmol). The mixture was stirred at room temperature for 3 h. Additional 1-methylpiperazine (0.064 mL, 0.572 mmol) and sodium triacetoxyborohydride (71 mg, 0.334 mmol) were added and the mixture was stirred at room temperature for 1 h. The reaction mixture was transferred to a separatory funnel containing saturated aqueous NaHCO3 solution (5 mL). The aqueous layer was extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with brine (5 mL), dried over MgSO4, filtered and concentrated. The product, t-butyl 1-(4-(2-methylpentyloxy)phenyl)-2-(4-methylpiperazin-1-yl)ethylcarbamate, was used directly in the next step: LRMS (ESI) m/e 420.3 [(M+H)+, calcd for C24H42N3O3 420.3].

Provenance & Evidence