Triphenylphosphine → (3R)-1-(Benzyloxy)-3-butylazetidin-2-one

Participants

Reaction Steps

To a solution of (2R)-2-(hydroxymethyl)-N-[(phenylmethyl)oxy]hexanamide (6) (52 g, 0.21 mol) and Ph3P (60 g, 0.23 mol) in THF (1500 mL) at 0° C. was added DIAD (41.8 g, 0.21 mol). The mixture was warmed up to rt and stirred overnight. TLC indicated completion of the reaction. THF was removed under vacuum. The residue was titurated with ethyl acetate/petroleum ether (1:10) and filtered. The filtrate was concentrated and the residue was purified by flash column chromatography to provide the title compound (52.8 g, 110%). LCMS: (M+H)+: 234.2.

Provenance & Evidence