2-Bromobutanoic acid → 4-(2-Bromobutanoyl)morpholine

To a solution of 2-bromobutanoic acid (0.3 mL, 2.81 mmol) in N,N-dimethylformamide (14 mL) are added morpholine (0.3 mL, 3.44 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (650 mg, 3.39 mmol) and 7-hydroxybenzotriazole (456 mg, 3.38 mmol), and the mixture is stirred at room temperature for 4.5 hours. After the reaction is completed, water is added to the mixture, and the mixture is extracted with ethyl acetate. The organic layer is washed with 1N-hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution, and a saturated brine, and dried over anhydrous magnesium sulfate. The solvent is evaporated, and the obtained residue is purified by silica gel column chromatography (n-hexane/ethyl acetate=3/1) to give the title compound (323 mg, yield: 49%).

1. extractionthe mixture is extracted with ethyl acetate
2. washThe organic layer is washed with 1N-hydrochloric acid
3. dry with materiala saturated aqueous sodium hydrogen carbonate solution, and a saturated brine, and dried over anhydrous magnesium sulfate
4. customThe solvent is evaporated
5. customthe obtained residue is purified by silica gel column chromatography (n-hexane/ethyl acetate=3/1)

ORD record

ord-ece91026f1e94536a417fff1f33f8abf

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07217724B2