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

Participants

Reaction Conditions

Reaction Steps

General procedure D was used to deprotect 0.4 grams (2.05 mmols) of 28 using 21 mL of dichloromethane and trifluoroacetic acid. After standard work-up procedures, the TFA salt of 28 was coupled to 0.6 grams (2.05 mmols) of 4-dodecylbenzoic acid using 1.1 grams (2.05 mmols) of PyBOP and 1.1 grams (8.2 mmols) of N,N-diisopropylethylamine in 21 mL of dichloromethane according general procedure E and heating to 50° C. After previously described work-up and purification procedures (column chromatography, 25% EtOAc in hexanes), 0.17 grams (0.45 mmols, 22%) of the title product was recovered as an off-white solid. 1H NMR (500 MHz, CDCl3) δ 7.50 (d, J=8.0 Hz, 2H), 7.22 (d, J=7.6 Hz, 2H), 4.96-4.84 (m, 1H), 3.73-3.63 (m, 1H), 5.62-3.52 (m, 1H), 2.68-2.58 (m, 2H), 2.39-2.26 (m, 1H), 2.24-2.10 (m, 1H), 2.06-1.96 (m, 1H), 1.67-1.55 (m, 1H), 1.39-1.18 (m, 18H), 0.87 (t, J=6.9 Hz, 3H). 13C NMR (126 MHz, CDCl3) δ 170.18, 146.28, 128.40, 127.61, 127.17, 118.73, 49.51, 46.87, 35.84, 31.91, 31.20, 30.30, 29.65, 29.56, 29.46, 29.34, 29.23, 25.58, 22.68, 14.12.

Provenance & Evidence