Dimethyl Sulfoxide → tert-Butyl 3-(2-oxoethyl)azetidine-1-carboxylate

To a solution of oxalyl chloride (488 μl, 5.58 mmol) in 40 ml dichloromethane at −78° C. was added dimethyl sulfoxide (792 μl, 11.16 mmol) dropwise by syringe. The mixture was stirred for 15 minutes at −78° C. when a solution of tert-butyl 3-(2-hydroxyethyl)azetidine-1-carboxylate (936 mg, 4.65 mmol) in 10 ml dichloromethane was added dropwise by syringe. After 1 hour at −78° C., triethylamine (3241 μl, 23.25 mmol) was added and the suspension was warmed to room temperature and stirred for an additional hour. The mixture was quenched with water (25 ml) and saturated aqueous potassium carbonate (10 ml), stirred vigorously and separated. The aqueous layer was extracted with dichloromethane (2×20 ml) and the combined organic layers were dried with magnesium sulfate, filtered and concentrated. The crude material was flash chromatographed to give the title compound.

1. additionwas added dropwise by syringe
2. customThe mixture was quenched with water (25 ml) and saturated aqueous potassium carbonate (10 ml)
3. stirringstirred vigorously
4. customseparated
5. extractionThe aqueous layer was extracted with dichloromethane (2×20 ml)
6. dry with materialthe combined organic layers were dried with magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customchromatographed

ORD record

ord-9252ec245fb54af1924baf08d272b632

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09302989B2