(1R,2S)-N-Pyrrolidinylnorephedrine

Abstract

[127641-25-2] C13H19NO (MW 205.30) InChI = 1S/C13H19NO/c1-11(14-9-5-6-10-14)13(15)12-7-3-2-4-8-12/h2-4,7-8,11,13,15H,5-6,9-10H2,1H3/t11-,13+/m1/s1 InChIKey = FZVHJGJBJLFWEX-YPMHNXCESA-N (chiral ligand for the enantioselective addition of dialkylzinc reagents to aromatic and aliphatic aldehydes, alkynes to aromatic aldehydes, and lithium acetylides to an aromatic ketone) Alternate Name: (1R,2S)-1-phenyl-2-(1-pyrrolidinyl)-1-propanol, [R-(R*,S*)]-β-methyl-α-phenyl-1-pyrrolidine ethanol. Physical Data: mp 45–46 °C, [α]D25 + 15 (c 2, CHCl3). Solubility: soluble in heptane and toluene. Form Supplied in: off-white crystalline solid. Analysis of Reagent Purity: H-NMR, C-NMR, elemental analysis. Preparative Methods: the title reagent is prepared1 by the treatment of (1R, 2S)-(−)-norephedrine with 1,4-dibromobutane and NaHCO3 in toluene. This approach can be modified to form a wide variety of cyclic and acyclic tertiary amine derivatives. The enantiomeric reagent has also been formed from ( + )-norephedrine. Purification: the hydrochloride salt can be precipitated from toluene solution, and the free base is dissolved in heptane upon treatment with NaOH. Concentration and cooling of the cold heptane solution affords the crystalline solid. Handling, Storage, and Precautions: no particular precautions are recommended for this relatively safe compound.