(1,1'-Biphenyl)-2-carboxaldehyde → HCID 89527718, compound

Participants

Reaction Steps

Biphenyl carboxaldehyde (2.82 g, 15.5 mmol) was added to a stirred solution of (1R,3S)-3-aminocyclopentanecarboxylic acid (2.0 g, 15.5 mmol) in anhydrous methanol (50 mL) and acetic acid (2 mL). After stirring at room temperature for 1 hour, sodium triacetoxyborohydride (6.57 g, 31 mmol) was added portion wise over 10 minutes and the reaction was stirred at room temperature for 4 hours, diluted with saturated aqueous sodium chloride, and extracted with ethyl acetate (3×30 mL). The combined organic phase was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give crude (1R,3S)-3-(biphen-4-ylmethyl-amino)-cyclopentane carboxylic acid, which was used in the next step without further purification; m/z for C19H21NO2 expected 295.2. found 318.1 (M+Na)+, 296.3 (M+H)+.

Provenance & Evidence