N,1-diphenylethan-1-imine → N-(1-Phenylethyl)aniline

반응식

CC(C)([O-])C.[K+].[C:7]1([C:13](=[N:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(O)(C)C.[Ru+2]>[C:16]1([NH:15][CH:13]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH3:14])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

참가 물질

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온도: 60 °C

실험 절차

The reaction was carried out in a multiwell hydrogenation vessel. Dichloro-{1,2-Bis[(2R,5R)-2,5-diphenylphospholano]methane}[(1S,2S)-1,2-diphenylethylenediamine)] ruthenium (II) (2.2 mg, 0.0025 mmol) was suspended in degassed isopropanol (2 ml) in a Schlenk flask under nitrogen. Added potassium tert-butoxide (1M in tert-butanol, 0.025 ml) and heated until a yellow solution was obtained. The glass liner was charged with N-(1-phenylethylidene)aniline (98 mg, 0.50 mmol). Charged to 10 bar nitrogen and vented (×5). Added the precatalyst solution and charged to 10 bar nitrogen and vented (×2). Commenced stirring at 1000 rpm and heated to 60° C. Charged to 10 bar H2 and stirred for 18 h. Cooled to room temperature, vented and evaporated to give phenyl-(1-phenylethyl)amine, conversion>99%, ee 71% (GC, sample derivatised by treatment with acetic anhydride pyridine, Chirasil DEX CB, 25 m×0.25 mm, injector/detector 200° C., helium 20 psi, 140° C. for 20 minutes then ramp at 5° C./min to 200° C., hold for 5 minutes, retention times 23.21 minutes and 23.45 minutes).