Tributylphosphine → HCID 18536080, compound

Participants

Reaction Steps

To a solution of di-tert-butylazodicarboxylate (5.557 g, 24.1 mmol) in 20 mL of EtOAc at 0° C. was added tributylphosphine (6.013 mL, 24.1 mmol) dropwise. After 10 minutes, a solution of the product from Step D (6.8548 g, 16.09 mmol) in 10 mL of EtOAc was added dropwise over 15 minutes, and the reaction was allowed to warm to room temperature. After one hour, the solution was poured into EtOAc, washed with sat. aq. NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product mixture was taken up in 30 mL of ether, 1N HCl/Ether was added (17 mL), and the solution was concentrated in vacuo. This was stirred in 50 mL of cold isopropanol over an ice bath for 30 minutes, and the resulting slurry was filtered and rinsed with cold isopropanol. The filtered solid was dried in vacuo next to P2O5 to provide the titled product as a white solid.

Provenance & Evidence