Nitrogen → N-tert-butoxycarbonyl-4-(pyrrolidin-1-yl)pentan-1-amine

Participants

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of pyrrolidine (79 mg, 1.11 mmol) in dry CH3CN (6 mL) was added tert-butyl (4-oxopentyl)carbamate (291 mg, 1.44 mmol) followed by Na(OAc)3BH (680 mg, 2.88 mmol) at rt. The reaction mixture was stirred at rt until completion of the reaction. Sat. aq. NaHCO3 was then added and the mixture extracted with EA (3×). The combined org. extracts were dried over MgSO4, filtered and concentrated under reduced pressure. The crude residue was purified by FC(CH2Cl2-MeOH—NH3) to give pure N-tert-butoxycarbonyl-4-(pyrrolidin-1-yl)pentan-1-amine as a colorless oil. LC-MS-conditions 05c: tR=0.53 min; [M+H]+=257.41. The title compound was obtained after Boc deprotection using 4N HCl in dioxane (10.0 eq.) in CH2Cl2 at rt as a colorless oil.

Provenance & Evidence