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Stereoselective synthesis of norephedrine and norpseudoephedrine by using asymmetric transfer hydrogenation accompanied by dynamic kinetic resolution.

The Journal of organic chemistry (2012-05-25)
Hyeon-Kyu Lee, Soyeong Kang, Eun Bok Choi
ABSTRACT

Each of the enantiomers of both norephedrine and norpseudoephedrine were stereoselectively prepared from the common, prochiral cyclic sulfamidate imine of racemic 1-hydroxy-1-phenyl-propan-2-one by employing asymmetric transfer hydrogenation (ATH) catalyzed by the well-defined chiral Rh-complexes, (S,S)- or (R,R)-Cp*RhCl(TsDPEN), and HCO(2)H/Et(3)N as the hydrogen source. The ATH processes are carried out under mild conditions (rt, 15 min) and are accompanied by dynamic kinetic resolution.

MATERIALS
Product Number
Brand
Product Description

Supelco
(±)-Phenylpropanolamine hydrochloride solution, 1.0 mg/mL in methanol (as free base), ampule of 1 mL, certified reference material, Cerilliant®
Sigma-Aldrich
(1S,2R)-(+)-Norephedrine, 98%
Sigma-Aldrich
(1S,2S)-(+)-Norpseudoephedrine, ≥98.0% (NT)
Sigma-Aldrich
Cathine hydrochloride
Sigma-Aldrich
DL-Norephedrine hydrochloride, ≥99%
Supelco
(+)-Norpseudoephedrine hydrochloride solution, 100 μg/mL in methanol (as free base), ampule of 1 mL, certified reference material, Cerilliant®