Sodium hydride → 3-Butoxy-3-phenyl-1-(tert-butoxycarbonyl)azetidine

Participants

Reaction Conditions

Reaction Steps

A solution of 1 g (4.0 mmol) of 3-hydroxy-3-phenyl-1-(tert-butoxycarbonyl)azetidine dissolved in 5 ml of DMF is added dropwise to a suspension of 300 mg of 60% NaH in 3 ml of DMF, immersed in a bath at 0° C. 2.5 ml of n-iodobutane are added dropwise. The reaction medium is left to stir at 0° C. for 15 minutes and 72 hours at ambient temperature. The medium is hydrolysed by addition of a saturated solution of ammonium chloride, followed by extraction with ethyl acetate. The organic phase is dried and evaporated to dryness. The crude product obtained is purified on silica in a 7/3 heptane/ethyl acetate mixture. 500 mg in the form of a light yellow oil are obtained with a yield of 41%.

Provenance & Evidence