Benzenepropanal → Benzyl 6-(3-phenyl-1-hydroxypropyl)-3-(2-azidoethyloxy)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Participants

Reaction Steps

A solution of benzyl 3-(2-azidoethyloxy)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate (66 mg) in anhydrous THF (0.5 ml) is added dropwise over 5 mins to a stirring solution of lithium diisopropylamide (from 31 μl diisopropylamine and 140 μl 1.6N BuLi) in anhydrous THF (3.5 ml) at -78°. After stirring an additional 15 mins at -78° under N2, the solution is treated with 3-phenylpropionaldehyde (134 mg, 5 equivalents) in THF (0.5 ml). After 5 more mins at -78°, the solution is treated with saturated aqueous NH4Cl (3 ml) and allowed to warm to room temperature. The mixture is diluted with EtOAc (50 ml), washed with water (3×10 ml) and brine, dried with MgSO4, filtered, and evaporated in vacuo. The residue is chromatographed on silica gel to yield benzyl 6-(3-phenyl-1-hydroxypropyl)-3 -(2-azidoethyloxy)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

Provenance & Evidence