Ethoxyacetic acid → HCID 9932172, compound

Participants

Reaction Steps

To a stirred solution of 4-amino-1-[(9S,10S)-2-chloro-9,10-dihydro-9,10-methanoanthracene-9-ylmethyl]piperidine (752 mg, 2.22 mmol), dimethylaminopyridine (542 mg, 4.44 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (848 mg, 4.44 mmol), in methylene chloride (15 mL) was added ethoxyacetic acid (0.25 mL, 2.44 mmol). After stirring for 18 h, the mixture was treated with 1N sodium hydroxide (75 mL), and extracted with methylene chloride (3×75 mL). The combined extracts were washed with 1N sodium hydroxide (2×75 mL) and brine (50 mL), dried (sodium sulfate), filtered and concentrated to give a milky white syrup. Chromatography of this material over silica gel (eluant: ethyl acetate) provided the title compound as a colorless glass (807 mg, 86%), mp 68.0°-70.0° C.; MS(CI): 425 (M+H); [α]D23 =+41° (c=0.01, CHCl3); NMR (300 MHz,DMSO-d6): 1.13(t, 3H, J=7.0 Hz), 1.49(m, 2H), 1.61(m, 2H), 2.26(m, 2H, J=11.9 Hz), 2.46(br s, 2H), 2.94(m, 2H), 3.33(m, part. submerged, 2H), 3.43(q, 2H, J=7.0 Hz), 3.62(m, 1H), 3.78(s, 2H), 4.33(s, 1H), 6.94(m, 3H), 7.23(br m, 4H), 7.48(d, 1H, J=8.3 Hz).

Provenance & Evidence