Water → 1-(Diphenylmethyl)azetidin-3-one

Temperature

-78 °C

A three-neck flask was charged with oxalyl dichloride (10.6 mL, 119 mmol) and DCM (100.00 ml, 306 mmol), and the solution was cooled to −78° C. To the stirred solution was added, via dropping funnel, dimethylsulfoxide (16.9 mL, 238 mmol) in DCM (50 mL) over 30 min. The reaction was stirred at −78° C. for an additional 5 min, and then 1-benzhydrylazetidin-3-ol (25.90 g, 108 mmol) in DCM (50 mL) and DMSO (10 mL) was added dropwise over 5 min (T was maintained <−60° C.). The solution was stirred at −78° C. for an additional 20 min, and Et3N (75.3 mL, 541 mmol) was added slowly. The reaction was allowed to reach room temperature over 30 min and water (200 mL) was added. The mixture was extracted with EtOAc, washed with brine, dried over MgSO4 and evaporated. Purification by flash chromatography using 2% Et3N/hexanes gave 1-benzhydrylazetidin-3-one. 1H NMR (300 MHz, CDCl3) δ ppm 7.41-7.52 (m, 4H), 7.26-7.35 (m, 4H), 7.16-7.26 (m, 2H), 4.59 (s, 1H), 3.90-4.07 (m, 4H).

1. additionTo the stirred solution was added
2. temperature(T was maintained <−60° C.)
3. stirringThe solution was stirred at −78° C. for an additional 20 min
4. waitto reach room temperature over 30 min
5. extractionThe mixture was extracted with EtOAc
6. washwashed with brine
7. dry with materialdried over MgSO4
8. customevaporated
9. customPurification by flash chromatography

ORD record

ord-119d50933ee7427b814d6010d04cd67c

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07919519B2