3-azetidinecarboxylic Acid → HCID 67167733, compound

Participants

Reaction Conditions

Reaction Steps

To 3-(4-propylphenyl)-4,5-dihydronaphtho[2,1-d]isoxazole-7-carbaldehyde (Preparation 20E, 0.191 g, 0.602 mmol) in dichloroethane (2 mL) and methanol (2.0 mL) was added azetidine-3-carboxylic acid (0.073 g, 0.722 mmol) and 8 drops of acetic acid. The reaction mixture was heated at 80° C. for 1.5 h. The reaction mixture was cooled to room temperature and sodium cyanoborohydride (0.045 g, 0.722 mmol) was added in one lot. The reaction mixture was stirred at room temperature for 20 min., and then concentrated. Acetonitrile (10 mL) was added to the resulting residue. The contents were sonicated for ˜2 min. and filtered. The solid was washed with acetonitrile (2×10 mL), water (2×10 mL), acetonitrile (5 mL), and dried to yield 1-((3-(4-propylphenyl)-4,5-dihydronaphtho[2,1-d]isoxazol-7-yl)methyl)azetidine-3-carboxylic acid as a grey solid (90 mgs). The compound had an HPLC retention time=3.08 min (condition C); LC/MS M+1=403.

Provenance & Evidence