3-Chlorophenol → tert-Butyl (2S)-2-[(3-chlorophenoxy)methyl]pyrrolidine-1-carboxylate

Participants

Reaction Steps

A solution of diisopropyl azodicarboxylate (1.4 mL, 7.1 mmol) in THF (3.5 mL, 44 mmol) was slowly added to a 0° C. solution of BOC-PRO-OL (1.0 g, 5.0 mmol), 3-chlorophenol (0.68 g, 5.2 mmol) and triphenylphosphine (1.5 g, 5.8 mmol) in THF (17 mL, 210 mmol). The reaction mixture was warmed to ambient temperature. After 3 h the reaction mixture was quenched with 1 N NaOH and extracted with methylene chloride (3×). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified on the Isco (120 g cartridge, hexanes to ethyl acetate).

Provenance & Evidence