3-azetidinecarboxylic Acid → HCID 67170299, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(2-(1-(4-fluorophenyl)cyclohexyl)ethyl)naphtho[1,2-d]oxazole-7-carbaldehyde (Preparation 42E, 47.0 mg, 0.117 mmol) in dichloroethane (1 mL) and methanol (1 mL) was added azetidine-3-carboxylic acid (23.66 mg, 0.234 mmol) followed by 2 drops of acetic acid. Next, the reaction mixture was stirred in a 60° C. in an oil bath for 1 hr. After cooling to room temp sodium cyanoborohydride (14.71 mg, 0.234 mmol) was added, and the mixture was stirred at room temperature overnight. Next, the reaction mixture was placed on a Combiflash column (12 g silica gel) filled with 7:93 methanol-dichloromethane, and eluted with 2:8 followed by 3:7 and 1:1 MeOH—CH2Cl2 to give the 1-((2-(2-(1-(4-fluorophenyl)cyclohexyl)ethyl)naphtho[1,2-d]oxazol-7-yl)methyl)azetidine-3-carboxylic acid as a brown solid. LC/MS M+1=487.31; 1H NMR (400 MHz, CDCl3) δ ppm 8.31 (1H, d, J=8.36 Hz), 7.81 (1H, s), 7.58 (1H, d, J=9.02 Hz), 7.50 (1H, d, J=8.80 Hz), 7.46 (1H, d, J=9.02 Hz), 7.24-7.31 (2H, m), 6.98 (2H, t, J=8.69 Hz), 4.03 (2H, br. s.), 3.79-3.96 (4H, m), 3.31 (1H, br. s.), 2.51-2.60 (2H, m), 2.00-2.14 (4H, m), 1.29-1.65 (8H, m).

Provenance & Evidence