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Pictet-Spengler route to Praziquantel
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27th July 2012 @ 01:32
START: 26/07/12 FINISH: 26/07/12 [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 (KAB26-20) -[/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]R[/i])-[1,1'-binaphthalene]-2,2'-diol (([i]R[/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][u]Summary and Conclusion[/b][/u] [b][u]References[/b][/u] [1] D. Bradley, G. Williams and M. Lawton, [i]J. Org. Chem.[/i] [b]2010[/b], [i]75[/i], 8351. DOI: 10.1021/jo101589h [url=http://dx.doi.org/10.1021/jo101589h]Paper[/url]. [2] H. Ishitani and S. Kobayashi, [i]TetLett[/i] [b]1996[/b], [i]37[/i], 7357. [3] S. Watanabe, Y. Kobayashi, T. Arai, H. Sasai, M. Bougauchi and M. Shibaski, [i]TetLett[/i] [b]1998[/b], [i]39[/i], 7353. [4] Rare-Earth Metal Triflates in Organic Synthesis, S. Kobayashi, M. Sugiura, H. Kitagawa and W. W.-L. Lam, [i]Chem. Rev.[/i] [b]2002[/b], [i]102[/i], 2227–2302. DOI: 10.1021/cr010289i [url=http://dx.doi.org/10.1021/cr010289i]Paper[/url]. ------------------------------------------ NOTES ------------------------------------------
Comments
Re: Yb(OTf)3/BINOL catalysed asymmetric acyl-PS formation of KAB26-20 by Murray Robertson
30th July 2012 @ 01:51
On the Monday morning - 4 days after the solution was made up - the flask that contained the Yb(OTf)3/BINOL mixture in THF had reduced in volume due to evaporation (flask still sealed with a septum) and nice, clear square pyramidal crystal had formed.

From%20KAB26-20%20-%20Yb%28OTf%293BINOL%

Washing with hexane (4 mL) caused slight precipitation so the mixture was washed with Et2O (4 ml) - this maybe resulted in slight loss of crystals but two or three larger (2-3 mm) crystals were fished out and dried under vacuum.
Re: Yb(OTf)3/BINOL catalysed asymmetric acyl-PS formation of KAB26-20 by Murray Robertson
1st August 2012 @ 02:06
Single crystal x-ray diffraction confirmed the crystals as (R)-BINOL