Benzyl Bromide → 3-(Phenylmethoxy)azetidine

tert-Butyl 3-hydroxyazetidine-1-carboxylate (3.0 g) was mixed with THF (30 ml), and sodium hydride (55% suspended in oil) (600 mg) was added thereto, followed by stirring at room temperature for 10 minutes. Benzyl bromide (2.5 ml) was added thereto, followed by stirring at room temperature for 3 hours. Water and EtOAc were added to the reaction mixture, and the organic layer was dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was mixed with DCE (30 ml), and TFA (15 g) was added thereto, followed by stirring at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure and purified by basic silica gel column chromatography (CHCl3/MeOH) to obtain 3-(benzyloxy)azetidine (2.2 g).

1. additionwas added
2. stirringby stirring at room temperature for 3 hours
3. dry with materialthe organic layer was dried over Na2SO4
4. concentrationconcentrated under reduced pressure
5. additionThe obtained residue was mixed with DCE (30 ml), and TFA (15 g)
6. additionwas added
7. stirringby stirring at room temperature for 3 hours
8. concentrationThe reaction mixture was concentrated under reduced pressure
9. custompurified by basic silica gel column chromatography (CHCl3/MeOH)

ORD record

ord-2ab5bf51c305450fa0e7c63f01bf182f

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08716470B2