Toluene → HCID 58843203, compound

Participants

Reaction Conditions

Reaction Steps

[(Z)-(S)-1-Benzyl-3-(2-pyrrolidin-1-yl-ethylcarbamoyl)-allyl]-carbamic acid tert-butyl ester. To a solution of (Z)-(S)-4-tert-butoxycarbonylamino-5-phenyl-pent-2-enoic acid methyl ester (0.10 g, 0.33 mmol) in toluene (3.6 mL) was added aminoethylpyrrolidine (0.041 g, 0.36 mmol) and trimethylaluminum (2 M in hexanes, 0.026 g, 0.36 mmol), and the solution was stirred (25° C., 4 h). The solvent was removed in vacuo, and the residue was partitioned with 1 N NaOH and CH2Cl2 (50 mL each). The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. The resulting residue was purified by column chromatography using 0–20% (1% NH4OH/MeOH in CH2Cl2) to provide the desired product as a clear oil (0.02 g, 16%): MS (electrospray): mass calculated for C22H33N3O3, 387.25; m/z found, 388.2 [M+H]+; 410.2 [M+Na]+. 1H NMR (CDCl3, 400 MHz): 7.20–7.25 (m, 2H), 7.13–7.18 (m, 3H), 5.72–5.81 (m, 2H), 5.08 (br s, 1H), 4.94 (br s, 1H), 3.28–3.45 (m, 2H), 2.91 (dd, J=13.4, 5.6 Hz, 1H), 2.77–2.86 (m, 1H), 2.51–2.61 (m, 2H), 2.42–2.47 (m, 4H), 1.65–1.71 (m, 4H), 1.32 (s, 9H).

Provenance & Evidence