2-Chloroaniline → 1-tert-Butyl 2-methyl 2-{2-[(2-chlorophenyl)amino]ethyl}pyrrolidine-1,2-dicarboxylate

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Reaction Steps

A solution of 1-tert-butyl 2-methyl 2-(2-oxoethyl)pyrrolidine-1,2-dicarboxylate (220 mg, 0.00081 mol) in DCM (anhydrous, 4 mL) was added to 2-chloroaniline (110 μL, 0.0010 mol) and the resulting solution was stirred for 20 min. Sodium triacetoxyborohydride (290 mg, 0.0014 mol) was then added to the mixture. After stirring at RT for 12 h, the reaction mixture was diluted with EtOAc and quenched by the addition of water. The crude mixture was filtered through a pad of diatomaceous earth and the filter pad were washed several times with EtOAc and the resulting layers were of the filtrate separated. The aqueous phase was extracted with EtOAc (3×10 mL) and the combined organic phases were washed with brine (2×5 mL). The organic phase was then dried (NaSO4), filtered, and concentrated in vacuo to afford the desired product. LC-MS: 327.1 (M−Boc+2H)+ and 383.2 (M+1H)+.

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