The synthesis of new chiral quartener amonium compounds which were potential for resolution of BINOLs

In the present study, four new chiral quarterner amonium compounds were synthesized as potential resolving agents for resolution of racemik BINOL.For this purpose, L- phenylalanine and L- phenylglycine were reduced to their aminoalcohol derivatives according to literature procedure.Treatment of L-phenylalaninol, L- phenylglycinol and commercial (1S,2R)-2 amino-1,2-diphenylethanol with bis-(2-chloroethyl) ether in the presence of pentametyl piperidine resulted in dialkylation of the amine nitrogen to afford M1, M2, M3. And treatments of tertiary amines M2 and M3 with HCl (1 eq) gave their hydrochloride salts M2-HCl, M3-HClThen, these N-morpholine aminoalcohols (M1, M2, M3) were reacted with methyl iodide at room temperature in order to obtain new chiral quartener amonium compounds QM1, QM2, QM3 .And transformation of quartener amonium iodide (QM1), to chloride (QM1-Cl) was carry out.