Benzylamine → HCID 58293278, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(3-oxopropyl)pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (5.68 g) in tetrahydrofuran (57 ml) was added benzylamine (6.53 ml) at room temperature, and the mixture was stirred for 1 hour. The mixture was cooled to 0° C., and thereto was added sodium triacetoxyborohydride (5.07 g). The mixture was stirred at room temperature for 12.5 hours. To the reaction mixture were added water (12 ml) and saturated aqueous ammonium chloride solution (200 ml), and the mixture was extracted with n-hexane/ethyl acetate (1/2, 210 ml×2, 120 ml×2) 4 times. To the combined organic layer was added n-hexane (150 ml), and the mixture was extracted with 10% aqueous potassium bisulfate solution (180 ml×3) 3 times. The combined aqueous layer was neutralized by 4M aqueous sodium hydroxide solution to pH 7 to 8, and thereto was added saturated aqueous sodium bicarbonate solution (100 ml). The mixture was extracted with ethyl acetate (200 ml). The separated aqueous layer was extracted with ethyl acetate (200 ml×2) twice, and the combined organic layer was washed with saturated aqueous sodium chloride solution (200 ml). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the titled compound (7.69 g).

Provenance & Evidence