Benzyl Bromide → HCID 10587639, compound

Temperature

0 °C

tert-butyl 3-hydroxyazetidine-1-carboxylate (21) (1 gm, 5.77 mmol) was dissolved in dry DMF (15 ml) and was cooled to 0° C. under nitrogen and was added sodium hydride (0.35 gm, 8.66 mmol). The reaction mixture was allowed to stir at room temperature for 30 min and was added benzylbromide (22; 1.08 gm, 6.35 mmol) at 0° C. The reaction mixture was then allowed warm to room temperature and stirred for 2 h. After completion of the reaction it was quenched by the addition of sat. ammonium chloride solution and extracted with ether. The organic layer was then dried over sodium sulfate and concentrated under vacuum. The crude product was purified column chromatography to yield compound 23 (1.21 gm, 80%).

1. temperatureThe reaction mixture was then allowed warm to room temperature
2. stirringstirred for 2 h
3. customAfter completion of the reaction it
4. customwas quenched by the addition of sat. ammonium chloride solution
5. extractionextracted with ether
6. dry with materialThe organic layer was then dried over sodium sulfate
7. concentrationconcentrated under vacuum
8. customThe crude product was purified column chromatography

ORD record

ord-dc86bd3dbf8d40cb907073ef42ae42f4

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09388164B2