4-Fluorobenzaldehyde → HCID 69066592, compound

Participants

Reaction Conditions

Reaction Steps

cis-2-Amino-cyclooctanecarboxylic acid methyl ester (0.66 g, 3.56 mmol) was dissolved in methanol (20 mL). 4-Fluoro-benzaldehyde (0.44 g, 3.56 mmol) was added followed by acetic acid (1 mL). The solution was stirred at 25° C. for 10 min. Sodium cyanoborohydride (0.56 g, 8.9 mmol) was added and the mixture was stirred at 25° C. for 16 h. The mixture was poured into 1/2 saturated aqueous sodium bicarbonate solution (150 mL). The aqueous layer was extracted with ethyl acetate (2×150 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo to afford the crude product, cis-2-(4-fluoro-benzylamino)-cyclooctanecarboxylic acid methyl ester (0.7 g, 2.39 mmol, 67%), as a clear oil. LC-MS (ESI) calcd for C17H24FNO2 293.18, found 294.3 [M+H+].

Provenance & Evidence