Carbon Dioxide → HCID 58066376, compound

Participants

Reaction Steps

To a solution of 1-[4-Bromo-2-(methoxymethyl)phenyl]-2-methylpyrrolidine (16.5 g, 58 mmol) in anhydrous THF (160 mL) was added n-butyl lithium in drops at −78° C. After 3 hours at −78° C., the reaction mixture was poured onto crushed dry-ice (100 g). Once the excess carbon dioxide was escaped, the reaction mixture was evaporated, and then acidified with 1.5 N HCl. The precipitate was filtered off and washed with pet ether to afford title compound as a solid. LC/MS, M+(ESI): 249.9. 1H NMR (DMSO-d6, 400 MHz) δ 12.4 (1H, brs), 7.84 (1H, s), 7.70 (1H, d), 6.85 (1H, d), 4.32-4.42 (2H, m), 3.59-3.87 (1H, m), 3.56 (1H, m), 3.29 (3H, s), 3.13 (1H, m), 2.14 (1H, m), 1.89 (1H, m), 1.74 (1H, m), 1.55 (1H, m), 0.99 (3H, d).

Provenance & Evidence