Methyl iodide → HCID 59614369, compound

Participants

Reaction Steps

A solution of the crude (2R,4S)-4-[(3,5-bis-trifluoromethyl-benzyl)-(2H-tetrazol-5-yl)-amino]-2-ethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (52 mg, 0.10 mmol), methyl iodide (90 mg, 0.51 mmol) and potassium carbonate (28 mg, 0.20 mmol) in DMF (1.3 mL) is stirred at 50° C. for 2 hours. The reaction mixture is quenched with saturated ammonium chloride solution. The product is extracted three times with EtOAc. The combined organic layer is washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (eluent: n-hexane/EtOAc) to give (2R,4S)-4-[(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-2-ethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (45 mg, 44% overall yield in 4 steps).

Provenance & Evidence