(2s,3r)-1-(diphenylmethyl)-2-methylazetidin-3-ol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of racemic-(trans)-1-benzhydryl-2-methylazetidin-3-ol (0.198 g, 0.782 mmol) in THF (16 mL) was added iodomethane (98 μL, 1.6 mmol) and sodium hydride (0.035 g, 0.86 mmol, 60% in mineral oil). After 1.5 h, water was added and the mixture was extracted with EtOAc (3×). The combined organic phases were washed with brine, dried with sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified via FCC (0-15% EtOAc/n-heptanes) to give the title compound. MS (ESI+) m/z 268.2 (M+H)+. the mixture was extracted with EtOAc (3×) The combined organic phases were washed with brine dried with sodium sulfate filtered concentrated under reduced pressure The residue was purified via FCC (0-15% EtOAc/n-heptanes)

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 50 g (0.495 mol) of triethylamine are added to a solution of 77.33 g (0.329 mol) of trans-1-diphenylmethyl-3-hydroxy-2-methylazetidine in 600 ml of dichloromethane and the mixture is cooled to 0° C. The temperature is maintained, a solution of 50 g (0.437 mol) of mesyl chloride is added dropwise and the mixture is left for 24 hours at room temperature. The resulting solution is washed twice with water (300 ml), dried with anhydrous sodium sulphate and evaporated, and an oil is obtained which, when crystallized with petroleum ether, gives 104.6 g (96%) of trans-1-diphenylmethyl-2-methyl-3-methylsulphonyloxyazetidine, melting point 68°-71° C. The temperature is maintained The resulting solution is washed twice with water (300 ml) dried with anhydrous sodium sulphate evaporated an oil is obtained which, when crystallized with petroleum ether