Sodium Acetate → HCID 66981763, compound

To a solution of 3-bromo-2-ethylbenzaldehyde (2.66 g, 12.48 mmol) in Dichloromethane (DCM) (30 mL) were added methyl 3-azetidinecarboxylate (1.987 g, 13.11 mmol) and sodium acetate (1.536 g, 18.73 mmol). The mixture was stirred for 30 min at rt then sodium triacetoxyborohydride (3.97 g, 18.73 mmol) was added to above solution. The obtained mixture was stirred for an hour at rt. The solvent was removed under the reduced pressure, water (30 mL) was added to the above residue and the mixture was adjusted to pH value around 3 with HCl (1.0 N) then extracted with EtOAc (10 mL). Acidic phase was adjusted to pH value around 8 with NaOH (1.0 N) solution then extracted with EtOAc (30 mL). The organic phase was dried over anhydrous sodium sulfate, concentrated under the reduced pressure and dried in vacuum to give methyl 1-(3-bromo-2-ethylbenzyl)azetidine-3-carboxylate (3.04 g) as pale yellow oil

1. stirringThe obtained mixture was stirred for an hour at rt
2. customThe solvent was removed under the reduced pressure, water (30 mL)
3. additionwas added to the above residue
4. extractionthen extracted with EtOAc (10 mL)
5. extractionthen extracted with EtOAc (30 mL)
6. dry with materialThe organic phase was dried over anhydrous sodium sulfate
7. concentrationconcentrated under the reduced pressure
8. customdried in vacuum

ORD record

ord-27335f2f789542568684df7b4299c0a8

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08389508B2