Sodium Bicarbonate → 1-Benzhydryl-3-cyclopropylazetidin-3-ol

Participants

Reaction Conditions

Reaction Steps

To a 0.5 M cyclopropylmagnesium bromide in THF (4.72 mL, 2.36 mmol), 1-benzhydryl-azetidin-3-one (200 mg, 0.843 mmol) in THF (3 mL) was added dropwise at −78° C. The reaction mixture was stirred at −78° C. for 2 hr. Then it was added saturated NaHCO3 solution and extracted with ether (3×20 mL). The organic layers were combined, dried (MgSO4) and concentrated to give a light yellow oil. The crude product was purified by Prep. HPLC column using CH3CN—H2O-ammonium acetate solvent system. Fractions were collected and concentrated. Then it was extracted with ethyl acetate. The organic layers were combined, dried (MgSO4) and concentrated to give a colorless oil as Grignard reaction product. (63 mg, 27% yield).

Provenance & Evidence