Cesium carbonate → HCID 21034112, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (3S)-(+) -3-(tert-butoxycarbonylamino)pyrrolidine (410 mg, 2.20 mmol), in 22 mL EtOH, was added, (288 μL, 2.31 mmol) of 4-fluorobenzyl bromide, and (788 mg, 2.42 mmol) of finely powdered cesium carbonate. The stirred reaction mixture was heated at 80° C., under nitrogen for 3 h, after which time, TLC indicated the reaction was complete. The reaction was then concentrated in vacuo to about 5 mL, and was then diluted with 30 mL of EtOAc, and washed with 20 mL of 5% NH4OH. The aqueous fraction was extracted with diethyl ether (3×20 mL). The combined organics were washed with 20 mL of brine, dried (MgSO4), filtered and concentrated. The crude white solid was triturated with 1:1 ether-hexane to give 501 mg (77%) of the desired product as a white solid. 1H-NMR (400 MHz, CDCl3) δ7.2-7.3 (m, 2H), 6.9-7.1 (m, 2H), 4.85 (br. s, 1H, exchanges), 4.18 (br. s, 1H), 3.55 (s, 2H), 2.65 (br. m, 1H), 2.58 (n, 1H), 2.50 (m, 1H), 2.2-2.4 (m, 2H), 1.5-1.7, (m, 1H), 1.4 (s, 9H).

Provenance & Evidence