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24th July 2012 @ 14:06
START: 25/07/12 FINISH: [b][u]Hazard and Risk Assessment[/b][/u] [data]4712[/data] [b][u]Previous Experiments[/b][/u] [blog]6069[/blog] [blog]6168[/blog] [b][u]Chemical Information[/u][/b] [b]2-(3,4-dimethoxyphenyl)-N-(4-nitrobenzylidene)ethanamine (MNR42-1)[/b] - SMILES: O=[N+]([O-])C1=CC=C(/C=N/CCC2=CC(OC)=C(OC)C=C2)C=C1, InChI: InChI=1S/C17H18N2O4/c1-22-16-8-5-13(11-17(16)23-2)9-10-18-12-14-3-6-15(7-4-14)19(20)21/h3-8,11-12H,9-10H2,1-2H3/b18-12-, InChIKey: LMBMXYXQVBPKHJ-PDGQHHTCSA-N. [b]1-(6,7-dimethoxy-1-(4-nitrophenyl)-3,4-dihydroisoquinolin-2(1H)-yl)ethanone (KAB26-18) -[/b] SMILES: O=[N+]([O-])C1=CC=C(C2N(C(C)=O)CCC3=CC(OC)=C(OC)C=C32)C=C1, InChI: InChI=1S/C19H20N2O5/c1-12(22)20-9-8-14-10-17(25-2)18(26-3)11-16(14)19(20)13-4-6-15(7-5-13)21(23)24/h4-7,10-11,19H,8-9H2,1-3H3, InChIKey: OIFIJKJQAGAGKY-UHFFFAOYSA-N. [b]([i]S[/i])-[1,1'-binaphthalene]-2,2'-diol (([i]S[/i])-BINOL)[/b] - SMILES: OC1=[C@]([C@]2=C(C=CC=C3)C3=CC=C2O)C4=CC=CC=C4C=C1, InChI: InChI=1S/C20H14O2/c21-17-11-9-13-5-1-3-7-15(13)19(17)20-16-8-4-2-6-14(16)10-12-18(20)22/h1-12,21-22H, InChIKey: PPTXVXKCQZKFBN-UHFFFAOYSA-N. [b][u]Procedure[/b][/u] [i]NOTE: All THF was dried over microwave activated 3 Å molecular sieves (2.0-2.5 mm) >72 h prior to use. All acetonitrile was dried over microwave 3 Å molecular sieves (2.0-2.5 mm) >24 h prior to use.[1] All glassware used was dried overnight at 115 °C.[/i] [b]Catalyst Solution Preparation[/b] ([i]S[/i])-[1,1'-binaphthalene]-2,2'-diol (28 mg, 0.097 mmol, 3 equiv.) and Yb(OTf)3 (0.020 mg, 0.032 mmol, 1 equiv.) were dissolved in dried THF (0.5 mL) to give a chiral catalyst solution of 64 mM. To a mixture of 4 Å molecular sieves (~1.5 g) in MeCN (16 mL) was dissolved MNR42-1 (100 mg, 0.318 mmol, 1 equiv.). The mixture was cooled in an acetone ice bath (-10 °C) before the addition of acetyl chloride (0.04 mL, 0.6 mmol, 1.8 equiv.) and 2,6-lutidine (0.06 mL, 0.5 mmol, 1.6 equiv.). Yb(OTf)3
Attached Files
HRA KAB26-18
Scheme KAB26-18
Table KAB26-18