Triethylamine → HCID 57671194, compound

Participants

Reaction Conditions

Reaction Steps

cis-6-Amino-cyclohex-3-enecarboxylic acid ethyl ester hydrochloride (411.4 mg, 2 mmol) and anhydrous tetrahydrofuran (20 mL) were mixed to form slurry. Triethylamine (295 μL, 2.1 mmol), magnesium sulfate (685 mg), and 4-fluoro-benzaldehyde (450 μL, 4.1 mmol) were added at 25° C. and the resulted mixture was stirred at 25° C. for 16 h. The precipitated solid was filtered off and the filtrate was concentrated in vacuo at 25° C. to give an oil. This oil was dissolved in methanol (35 mL) and sodium borohydride (155 mg, 4.1 mmol) was then added portionwise at 25° C. The mixture was stirred at 25° C. for 1 h. Saturated aqueous sodium bicarbonate solution (15 mL) was added, extracted with ethyl acetate (3×40 mL) and the organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to afford the desired product, 6-(4-fluoro-benzylamino)-cyclohex-3-enecarboxylic acid ethyl ester (537.6 mg, 1.94 mmol, 96.9%). This crude product was directly used in next step without further purification. LC-MS (ESI) calcd for C16H20FNO2 277.2, found 278.2 [M+H+].

Provenance & Evidence