tert-Butyl Formate → (S)-2-[(S)-2-(4-Allyloxy-3-chloro-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

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Reaction Conditions

Reaction Steps

In a 25 mL round-bottomed flask, (S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (279 mg, 1.3 mmol, Eq: 1.00) and (S)-methyl 3-(4-(allyloxy)-3-chlorophenyl)-2-aminopropanoate (350 mg, 1.3 mmol, Eq: 1.00) were combined with DMF (6 mL) to give a colorless solution. HATU (986 mg, 2.59 mmol, Eq: 2.00) and Hunig's base (335 mg, 453 μL, 2.59 mmol, Eq: 2.00) were added. The reaction mixture was stirred at 25° C. for 20 h. The reaction mixture was poured into saturated aqueous NaHCO3 solution and extracted with DCM (2×). The organic layers were combined, washed with water (3×) and brine (1×). The organic layers were dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 20 g, n-heptane/AcOEt 3/1, 2/1) to yield a yellow oil (570 mg; 94%). m/z=467.2 [M+H]+; 367.1 [M+H-Boc]+.

Provenance & Evidence