Hydrochloric Acid → (S)-N-((R)-(4-isobutoxyphenyl)((R)-pyrrolidin-2-yl)methyl)-2-phenylpropanamide

Participants

Reaction Steps

(R)-tert-Butyl 2-((R)-(4-isobutoxyphenyl)((S)-2-phenylpropanamido)methyl)pyrrolidine-1-carboxylate (34.1 mg, 0.071 mmol) in hydrogen chloride (2M in diethyl ether) (355 mL, 0.710 mmol) was stirred at room temperature for 6 h then the solution was concentrated in vacuo. The residue was purified by HPLC (20%→100% acetonitrile/water with 0.1% TFA) to afford after preparing the free base, (S)-N-((R)-(4-isobutoxyphenyl)((R)-pyrrolidin-2-yl)methyl)-2-phenylpropanamide (4.6 mg, 0.012 mmol, 16.69% yield over two steps). 1H NMR (400 MHz, CDCl3) δ 7.40 (br s, 1H), 7.26-7.35 (m, 5H), 6.98 (d, J=8.56 Hz, 2H), 6.74 (d, J=8.81 Hz, 2H), 4.93 (t, J=7.18 Hz, 1H), 3.77 (q, J=7.05 Hz, 1H), 3.64-3.67 (m, 1H), 3.62 (d, J=6.55 Hz, 2H), 2.97-3.06 (m, 2H), 2.87-2.96 (m, 1 H), 1.96-2.09 (m, 1H), 1.67-1.83 (m, 3H), 1.53-1.57 (m, 1H), 1.50 (d, J=7.05 Hz, 3H), 0.97 (d, J=6.80 Hz, 6H); LRMS (ESI) m/e 381.30 [(M+H)+, calcd for C24H33N2O2 381.25].

Provenance & Evidence