(1S,2R)-(+)-Norephedrine → 1795-95-5

Benzoyl chloride in an amount of 349 mg (2.48 mmol) and triethylamine in an amount of 1.0 ml (7.3 mmol) were added into 10 ml of chloroform solution of the above-described 1-phenyl-2-aminopropanol in an amount of 465 mg (2.48 mmol). The resulting solution was stirred for 2 hours in ice bath and added with water to discontinue the reaction. After separation of the solution, the chloroform solution was dried with anhydrous magnesium sulfate and distilled out under reduced pressure to obtain 1-phenyl-2-benzoylaminopropane in crude state. The crude product was purified by means of silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain anti-isomer of 1-phenyl-2-benzoylaminopropanol in an amount of 705 mg (2.42 mmol) at a yield of 97%. The optical purity of said anti-isomer was determined by means of high performance liquid chromatography (ethanol:hexane 1:30, flow rate: 1.0 ml/min., chiralcell OJ) and was found to be 95% ee as the purity of the (1S, 2R)-isomer. The optical purity of the syn-isomer was also determined and the purity was found to be 90% ee as the purity of the (1S, 2S)-isomer.

1. customthe reaction
2. customAfter separation of the solution
3. dry with materialthe chloroform solution was dried with anhydrous magnesium sulfate
4. distillationdistilled out under reduced pressure

ORD record

ord-b53964c7e6da4efe8f556867d13e849d

Source dataset

uspto-grants-2002_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06410749B1