1,2-Diphenyl-2-Aminoethanols. I. Synthesis of some erythro-1,2-Diphenyl-2-Alkylaminoethanols

A Simple, Scalable Synthetic Route to (+)- and (−)-Pseudoephenamine

“…Two prior studies of the reduction of methylimino benzil explored the use of Raney nickel 5 and sodium borohydride 6 as reductants, and in each case ephenamine was reported to be the major or exclusive product. We are unaware of any reports of the reduction of methylimino benzil to form pseudoephenamine as the primary product.…”

“…4 Wheatley and co-workers first described the preparation of methylimino benzil (3) by the condensation of methylamine and benzil in methanolÀwater at 50 °C, reporting a yield of 84%. 5 In adapting this synthesis, we found that it is critical to use a fresh (commercial) 40 wt % solution of methylamine in water (such that the titer of the volatile methylamine reactant is accurate) and crystalline benzil as a coreactant. After the reactants are combined, we heat the heterogeneous mixture in an oil bath while stirring until an internal temperature of 50 °C is achieved and all solids are dissolved.…”

Convergent integration of two self-labor domino sequences: a novel method for the synthesis of oxazole derivatives from methyl ketones and benzoins

“…A slightly lower yield was obtained when the reaction time was prolonged to 6 h. Then, the reaction temperature was optimized to increase the reaction yield; thus indicating that 120 1C was the optimal temperature (Table 1, entries 9-12). Various amines including inorganic and organic ammonium salts were then screened in the presence of iodine in DMSO at 120 1C (Table 1, entries [13][14][15][16][17]. However, most of the ammonium salts were inactive in this reaction.…”

“…Subsequently, 7 is formed as a product after the addition of ammonium acetate to 5. 14 Then 9a or its enolizational isomer 10a is obtained from 7 and 8a. When 10a undergoes intramolecular nucleophilic reaction, 11a is obtained.…”

Probing concerted proton–electron transfer in phenol–imidazoles

“…These were prepared by condensation between 3,5-di-tert-butyl-2-hydroxybenzaldehyde and the corresponding benzil by using formamide or ammonium acetate in acetic acid [see supporting information (SI) Appendix]. The N-cyclohexyl-imidazole derivative HOAr-im Cy,H (Cy ϭ cyclohexyl) was prepared analogously by using the Ncyclohexylimine of benzil (22), and the N-methyl compound was synthesized by alkylation of HOAr-im H,H with CH 3 I, employing KOH in acetonitrile. The benzimidazole compounds, HOAr-im bz and HOAr-im bzCl2 were prepared by condensation of the benzaldehyde with 1,2-diaminobenzenes and subsequent oxidation with 1,4-benzoquinone (23).…”