Aminophenylethanols and Related Compounds

Abstract

The authors wish to express their thanks and gratitude to Messrs P. Sadtler and Son, Inc., Research Laboratories, Philadelphia, U.S.A., for kindly carrying out the infrared spectrograms. The infrared ABBASSIA, CAIRO, EGYPT measurements of Ia were also carried out by l l r , Nagib Doss, Chemistry Department, Ohio State University, E.S.A., t o whom we are highly indebted.A\minophen>-lethanuls of the types I and 11, and the corresponding halides were required as svnthetic intermediates. The alcohols of the type I were prepared by condensation of styrene oxide and secondary amines, while the alcohols of the type I1 were prepared by amination of 2-bromo-2-phenylethanol. Treatment of the alcohols I or 11 with thionyl chloride in ether afforded the identical chloride which in the instance of the isomeric pyrrolidino alcohols proved to be 1-(2-chloro-2-phenJ-lethyl)-pyrrolidine hydrochloride.

Rearrangement of β-amino alcohols via aziridiniums: a review

“…No matter which nucleophile is used, the attack of the aziridinium always occurs at C-2, thus producing amines H 0 0 (Scheme 33). 42 The first explanation for the rearrangement of 104 to 105 was the direct transformation of the chlorosulfite intermediate 107 to the rearranged b-chloro amine 108 (Scheme 34, path 1). A second explanation could be the formation of the aziridinium intermediate 109 issued from an intramolecular nucleophilic attack of the pyrrolidine ring at the carbon bearing the chlorosulfite in 107 (Scheme 34, path 2).…”

“…Whereas ester 123 was obtained as the major product (58% yield), the rearranged ester 122 was isolated in moderate yield (15%). 42 A concerted mechanism was proposed to explain the transformation of 104 to 122 via intermediate 124 (Scheme 39).…”

“…Whereas ester 123 was obtained as the major product (58% yield), the rearranged ester 122 was isolated in moderate yield (15%). 42 28 b-Amino alcohols possessing a quaternary center can also be rearranged under these conditions with almost no loss of chirality. (R)-N,N-Dibenzyl-2-allyl-2-phenylglycinol 127 was transformed to 128 in 63% yield when subjected to TFAA (2.0 equiv.)…”

Lipase catalysis in the optical resolution of 2-amino-1-phenylethanol derivatives

“…Compounds lb-d were prepared by the known method from styrene oxide and primary amine. 27 The reaction between l a and ethyl chloroformate in aqueous sodium carbonate produced compound le.3 Compound If was prepared by the modified method from benzyl chloroformate using toluene as the reaction medium. The Nmonoacylated compounds, which were used to follow the enzymatic acylation reactions, were prepared chemically using equivalent amounts of butyric anhydride and compounds l a 4 and 2a-d in toluene while the corresponding diacylated compounds were easily obtained by the same procedure in the presence of 4-dimethylaminopyridine (DMAP) as a catalyst. "…”

Local Anesthetics. I. Esters of 2-(Dialkylamino)-1-phenylethanols

“…Typical of the compounds studied were I and II, and the products prepared have been described in Tables I and II, respectively. RCOOCH(R4)CH2NR,R2.R3X (I) RCOOCH2CH(R4)NR1R2-R3X (II) (1) Paper I of this series, S. L. Shapiro, H. Soloway, E. Chodos and L. Freedman, This Journal, 81, 201 (1959),…”