1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (E)-methyl 2-oxo-1'-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[indoline-3,4'-piperidine]-5-carboxylate

Participants

Reaction Steps

To a solution of methyl 2-oxospiro[indoline-3,4′-piperidine]-5-carboxylate hydrochloride (400 mg, 1.46 mmol) in anhydrous CH2Cl2 (10 mL) was added (E)-3-(2-(trifluoromethyl)phenyl)acrylic acid (315 mg, 1.46 mmol), HOBt (394 mg, 2.92 mmol), EDCI (576 mg, 2.92 mmol) and DIEA (942 mg, 7.30 mol) at 0° C. and then stirred overnight at rt under N2. Then the reaction mixture was washed with 1 N aq HCl and water. The organic layer was dried over Na2SO4, filtered and concentrated to afford a residue, which was purified by preparative TLC to give (E)-methyl 2-oxo-1′-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[indoline-3,4′-piperidine]-5-carboxylate (328 mg, 49%). 1H NMR (CDCl3): 1.58 (m, 4H), 1.97 (m, 3H), 3.91 (m, 3H), 4.15 (m, 1H), 4.40 (m, 1H), 6.85 (m, 1H), 6.98 (m, 1H), 7.48 (m, 1H), 7.56 (m, 1H), 7.72 (m, 1H), 7.99 (m, 2H).

Provenance & Evidence