p-Octylbenzoic acid → 1-(4-Octylbenzoyl)pyrrolidine-2-carbonitrile

Participants

Reaction Steps

General procedure D was used to deprotect 19 (1.2 mmol, 0.24 g). The product was immediately carried on and coupled to 2 (1.2 mmol, 0.281 g) using general procedure F. After standard work up procedures the title product was recovered from flash chromatography to yield 0.238 g (0.76 mmol) after two steps. 1H NMR (500 MHz, CDCl3) δ 7.50 (d, J=8.1, 2H), 7.21 (dd, J=7.9, 14.6, 2H), 4.91 (s, 0.5H), 4.66 (s, 0.5H), 3.67 (s, 1H), 3.56 (s, 1H), 2.66-2.60 (m, 2H), 2.32 (s, 1H), 2.17 (s, 1H), 2.01 (s, 1H), 1.88 (s, OH), 1.60 (d, J=7.5, 2H), 1.28 (dd, J=7.5, 14.4, 10H), 0.87 (t, J=6.8, 3H). 13C NMR (126 MHz, CDCl3) δ 173.09, 146.33, 133.26, 132.60, 128.43, 128.21, 127.64, 127.44, 118.72, 59.24, 52.28, 50.05, 46.85, 35.84, 31.85, 31.19, 29.41, 29.22, 25.42, 22.64, 14.11.

Provenance & Evidence