3-Oxo-azetidine-1-carboxylic acid tert-butyl ester → Tert-butyl 3-(3-fluorophenyl)-3-hydroxyazetidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

1-Boc-3-azetidinone (500 mg, 2.77 mmol, available from Aldrich #696315) was dissolved in dry tetrahydrofuran (20 ml) under N2 atmosphere. The solution obtained was cooled at 0° C. and 3-Fluorophenylmagnesiumbromide (1M in THF) (3.33 ml, 3.33 mmol) was added dropwise under stirring. The reaction was warmed to room temperature and stirred overnight. The reaction mixture was diluted with NH4Cl sat. sol. (50 ml) and the organics were extracted with ethylacetate (3×50 ml). Collected organics after solvent evaporation afforded the title compound (D28) (783 mg)

Provenance & Evidence