Tributylphosphine → 2-{(2R)-1-[(4-Fluorophenyl)sulfonyl]aziridin-2-yl}ethanol

Participants

Reaction Steps

To a solution of 4-fluoro-N-[(1R)-3-hydroxy-1-(hydroxymethyl)propyl]benzene-sulfonamide (1 equiv) from step 2 in THF (20 mL/g) was added azodicarboxylic acid dipiperidide (1 equiv) followed by tri-n-butylphosphine (1 equiv) dropwise over 30 min. The reaction was stirred for 30 min then filtered. The filtrate was washed with THF and H2O (5 mL/g), then added to the resulting solution and stirred for 1 h. NaCl was added to separate the aqueous and organic layers. The layers were cut and the organic layer washed with brine, dried over MgSO4 and concentrated in vacuo. The crude product was triturated in MTBE and filtered. The resulting solution was concentrated and triturated in EtOAc/Hex (1:1) and then filtered. The resulting solution was then concentrated and purified by column chromatography with EtOAc/Hex 25-75% to give the desired material (77%) as a light yellow oil.

Provenance & Evidence