Triphenylphosphine → (3R)-3-(5-hexen-1-yl)-N-benzoxy-2-azetidinone

Participants

Reaction Steps

To a mixture of (2R)-2-(hydroxymethyl)-N-benzoxy-7-octenamide (1.51 g, 5.47 mmol) and triphenylphosphine (1.72 g, 6.56 mmol) in THF (50 mL) was added dropwise diisopropyl azodicarboxylate (1.3 mL, 6.56 mmol) at 0° C. The reaction mixture was stirred and allowed to warm to room temperature overnight. The reaction was then quenched with water (50 mL). The aqueous layer was extracted with EtOAc (50 mL×2). The combined organic layers were washed with brine, and dried over MgSO4. After removing the solvent under vacuum, the residue was purified by flash column chromatography (hexane:EtOAc 6/1) to provide the title compound. MH+260.

Provenance & Evidence