1-(Diphenylmethyl)azetidin-3-one → HCID 53767266, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-fluorophenylmagnesium bromide (7.0 mL, 1 .OM (Et2O)) in toluene (20 mL) at −78° C. under argon, was added, dropwise, a solution of 1-diphenylmethyl-3-azetidinone (3) (1.4 g) in toluene (30 mL) over 30 minutes. The mixture was stirred for 4 hours at −78° C. then warmed to room temperature and partitioned between aqueous ammonium chloride solution (50 mL) and diethyl ether (3×20 mL). The combined organic fractions were washed (water, brine), dried (Na2SO4) and concentrated in vacuo. Purification by flash column chromatography (20% ethyl acetate, hexane) gave 3-(4-fluorophenyl)-1-diphenylmethyl-3-azetidinol (15) (1.82 g). To a stirred solution of the free base (1.82 g) in ether (5 mL) was added dropwise a solution of oxalic acid (0.49 g) in acetone (1 mL). The mixture was stirred for 5 minutes then filtered to give the oxalate salt hemihydrate (2.23 g), m.p. 75° C. (acetone). Found: C, 66.71; H. 5.34; N, 3.04. C24H22FNOs.0.5H2O requires C, 66.67; H, 5.32; N, 3.17%.

Provenance & Evidence