Carbon tetrabromide → tert-Butyl (3S)-3-bromopyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of N-Boc-(R)-3-hydroxypyrrolidine (0.936 g, 5 mmol) in THF (25 mL) was added carbon tetrabromide (2.487 g, 7.50 mmol) followed by triphenylphosphine (1.967 g, 7.50 mmol). The resulting suspension was allowed to stir at 60° C. for 1 h. Insoluble material was filtered, and concentrated. The residue was purified by silica gel column chromatography with a gradient of EtOAc (5-30%) in hexanes to afford 72 (1.12 g, 90%) as a colorless oil. LRMS (ESI): calc. 249.0; found 271.9 (MNa)+.

Provenance & Evidence