Hydrochloric Acid → HCID 58572501, compound

With reference to Chirality, 2005, 17, 476-480, 1.06 M solution of diethyl zinc in hexane (18.6 ml, 19.7 mmol) was added dropwise under ice cooling to a solution of 1-[(S)-(2-methoxy phenyl){[(1S)-1-phenylethyl]amino}methyl]-2-naphthol (0.38 g, 0.99 mmol) in toluene (5 ml). The mixture was stirred at room temperature for 1 hour. After stirring, the mixture was added with 2-bromo-5-fluorobenzaldehyde (2.0 g, 9.85 mmol) under ice cooling and stirred at room temperature for 16 hours. The reaction solution was added with 1N aqueous hydrochloride solution and extracted with dichloromethane. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=5/1) to give the title compound as a transparent oily substance (1.81 g, yield 79%).

1. stirringAfter stirring
2. stirringstirred at room temperature for 16 hours
3. extractionextracted with dichloromethane
4. washThe organic layer was washed with saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. distillationThe solvent was distilled off under reduced pressure
7. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate=5/1)

ORD record

ord-b2731d4686864121adbdea09c6c21d22

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173631B2