Trifluoroacetic acid → (S)-1-(4-undecylbenzoyl)pyrrolidine-2-carbonitrile

Participants

Reaction Steps

General procedure D was used to deprotect 0.447 grams (2.3 mmols) of 28. After standard work-up procedures, general procedure E was used to couple 2.3 mmols of the TFA salt of 28 to 0.635 grams (2.3 mmols) of 4-undecylbenzoic acid at 50° C. After work-up, 0.334 grams (0.94 mmols, 41%) of the title product was isolated as a yellow solid by flash chromatography (25% EtOAc in hexanes). 1H NMR (300 MHz, CDCl3) δ 7.24 (dd, J=12.2, 4.4 Hz, 2H), 7.04 (t, J=7.7 Hz, 2H), 4.97 (s, 1H), 3.88 (s, 1H), 3.31 (dt, J=18.1, 9.0 Hz, 1H), 2.77-2.64 (m, 1H), 2.63-2.54 (m, 1H), 2.24-2.12 (m, 1H), 1.60 (dt, J=15.1, 7.3 Hz, 4H), 1.29 (d, J=10.9 Hz, 14H), 0.88 (t, J=6.7 Hz, 3H). 13C NMR (126 MHz, CDCl3) δ 169.97, 146.29, 128.42, 128.18, 127.63, 127.17, 118.73, 49.51, 46.85, 46.20, 35.84, 31.91, 31.20, 30.27, 29.64, 29.61, 29.56, 29.46, 29.33, 29.23, 25.57, 22.68, 14.12.

Provenance & Evidence