Pyrrolidine → HCID 24953409, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)-2-chloro-N-(2-chloro-5-((1-phenylethylamino)methyl)phenyl)acetamide 46 (0.397 g, 1.2 mmol) in THF (6 mL) was added pyrrolidine (3.0 mL, 36 mmol). The reaction mixture was heated to 50° C. for 30 min, cooled to room temperature, partially concentrated under reduced pressure, quenched with saturated NaHCO3, and diluted with EtOAc. The aqueous phase was extracted with EtOAc (3×) and the combined organic extracts were washed with brine (1×), dried over MgSO4, filtered, and concentrated in vacuo. Purification by flash column chromatography on silica gel (eluted with 1% to 10% MeOH in DCM) gave (R)—N-(2-chloro-5-((1-phenylethylamino)methyl)phenyl)-2-(pyrrolidin-1-yl)acetamide 47 (0.292 g, 67% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 1.36 (d, J=6.5 Hz, 3H), 1.83-1.91 (m, 4H), 2.68-2.79 (m, 4H), 3.33 (s, 2H), 3.58 (d, J=13.5 Hz, 1H), 3.64 (d, J=13.3 Hz, 1H), 3.81 (q, J=6.7 Hz, 1H), 6.98 (d, J=8.2 Hz, 1H), 7.23-7.37 (m, 7H), 8.38 (s, 1H), 9.93 (s, 1H). Mass spectrum: calculated for C21H26ClN3O 371.2. found 372.2 (M++1).

Provenance & Evidence