1-(Diphenylmethyl)azetidin-3-one → 3-(4-tert-Butylphenyl)-1-diphenylmethyl-3-azetidinol

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-tert-butylphenyhnagnesium bromide (11.5 mL, 2.0M (Et2O)) in toluene (50 mL) at −78° C. under argon, was added, dropwise, a solution of 1-diphenylmethyl-3-azetidinone (3) (5.0 g) in toluene (100 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 (3×50 mL). The combined organic fractions were washed (water, brine), dried (Na2SO4) and concentrated in vacuo. Recrystallisation from cyclohexane gave 3-(4-tert-butylphenyl)-1-diphenylmethyl-3-azetidinol (9) (6.23 g), m.p. 168-169° C. (cyclohexane). Found: C. 83.68; H, 7.97; N, 3.72. C26H29NO requires C, 84.06; H, 7.87; N, 3.77%.

Provenance & Evidence