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(S)-benzyl 4-oxo-2-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyrrolidine-1-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
96%
A solution of (S)-1-((benzyloxy)carbonyl)-4-ox- opyrrolidine-2-carboxylic acid (3.0 g, 11.40 mmol) in DMF (50 mE) was cooled to 0 C. with ice bath. To the solution was added EDC (2.84 g, 14.8 mmol) in three batches. The reaction mixture was stirred at 00 C. for 5 mi and treated with 3H-[1 ,2,3] -triazolo[4,5-b]pyridin-3-ol (1.71 g, 12.54 mmol) in two batches. The reaction mixture was stirred at 00 C. for 10 mi and treated with a solution of (R)-1,2,3,4-tetrahydronaphthalen-1 -amine (1.76 g, 11.97 mmol) in DMF(8 mE) and DIEA (6.0 mE, 34.2 mmol) at 00 C. The ice bathwas then removed and the reaction mixture was stirred at rtfor 3 h. The reaction mixture was diluted with ethyl acetate and brine. The aqueous layer was extracted with ethyl acetate twice. The organic layers were combined, washed with saturated aq. NaHCO3 solution, brine, 1 N HC1 solution, and brine successively. The organic layer was dried over MgSO4 and the filtrate was concentrated in vacuo to give the title compound (4.3 g, 96%) as a light yellow solid. MS(ESI) m/z 393.3 (M+H).