Methyl iodide → HCID 131731890, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of racemic (trans)-tert-butyl 3-(dimethylamino)-4-hydroxypyrrolidine-1-carboxylate (0.96 g, 4.17 mmol) in THF (40 mL) at 0° C. was added NaH (0.25 g, 6.25 mmol, 60% dispersion in mineral oil), and the reaction mixture was stirred at 0° C. for 10 min. Then, iodomethane (0.29 mL, 4.6 mmol) was added dropwise and the resulting mixture was stirred at room temperature for 18 h. The reaction mixture was quenched with sat aq NH4Cl and extracted three times with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated to provide racemic-(trans)-tert-butyl-3-(dimethylamino)-4-methoxypyrrolidine-1-carboxylate. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.84 (br. s., 1 H), 3.46-3.54 (m, 1 H), 3.25 (s, 3 H), 3.12-3.22 (obs m, 3 H), 2.72 (br. s., 1 H), 2.16 (s, 6 H), 1.39 (s, 9 H).

Provenance & Evidence