2-Aminoadamantane hydrochloride → HCID 24744047, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-aminoadamantane hydrochloride (120 mg, 0.64 mmol) and CDI (141 mg, 0.87 mmol) in anhydrous CH2Cl2 (4 mL) at 0° C. was added DIEA (374 mg, 2.90 mmol). The mixture was stirred at 0° C. for 1 h. A solution of compound 2-(2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)acetic acid (142 mg, 0.58 mmol) was added dropwise slowly. The mixture was stirred at rt overnight and concentrated to give the crude product. A portion of the crude product was purified by preparative HPLC to give 2-1′-((2-adamantyl)carbamoyl)-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)acetic acid (60 mg, 36%). 1H NMR: (400 MHz, CDCl3): δ=1.56-1.73 (m, 6H), 1.74-1.90 (m, 10H), 1.95 (m, 2H), 2.10 (m, 1H), 2.45 (m, 1H), 2.60 (m, 1H), 3.01 (m, 3H), 3.65 (m, 1H), 3.87-3.99 (m, 3H), 7.15-7.26 (m, 4H); LC-MS (4 min) tR=2.70 min, m/z=423 (M++1).

Provenance & Evidence