1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 25145196, compound

Participants

Reaction Steps

To a stirred solution of 4-(2,4-dichloro-phenoxy)-2,2-dimethyl-butyric acid (250 g, 0.902 mmol, prepared in a similar way as described in J. Am. Chem. Soc. 89, 2500-1 (1967)) in dry DMF (3 mL) was added HOBt (180 mg, 1.173 mmol) and EDAC (225 mg, 1.173 mmol). After stirring for 1 hr at room temperature, DIPEA (306 μL) and 4-amino-adamantan-1-ol (181 mg, 1.082 mmol) were added and the resulting mixture was stirred for 16 hrs. at room temperature. The volatiles were removed in vacuo and the residue was purified using prep. HPLC/MS affording 153 mg (40%) of the title compound as a solid. 1H NMR (400 MHz, CDCl3) □ 1.34 (s, 6H), 1.52 (q, 4H), 1.69-1.79 (m, 4H), 1.87 (d, 2H), 2.02-2.16 (m, 5H), 2.57 (br.s., 1H), 3.95-4.02 (m, 1H), 4.05 (t, 2H), 6.02 (d, 1H), 6.83 (d, 1H), 7.17 (dd, 1H), 7.35 (d, 1H).

Provenance & Evidence