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Pictet-Spengler route to Praziquantel
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27th July 2012 @ 02:32
START: 26/07/12
FINISH: 26/07/12




Hazard and Risk Assessment
HRA KAB26-18


Previous Experiments
Preparation of MNR42-1
Yb(OTf)3/PyBOX catalysed asymmetric acyl-PS formation of KAB26-17

Chemical Information
2-(3,4-dimethoxyphenyl)-N-(4-nitrobenzylidene)ethanamine (MNR42-1) - 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.
1-(6,7-dimethoxy-1-(4-nitrophenyl)-3,4-dihydroisoquinolin-2(1H)-yl)ethanone (KAB26-20) - 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.
(R)-[1,1'-binaphthalene]-2,2'-diol ((R)-BINOL) - 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.

Procedure
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.

Summary and Conclusion


References
[1] D. Bradley, G. Williams and M. Lawton, J. Org. Chem. 2010, 75, 8351. DOI: 10.1021/jo101589h Paper.
[2] H. Ishitani and S. Kobayashi, TetLett 1996, 37, 7357.
[3] S. Watanabe, Y. Kobayashi, T. Arai, H. Sasai, M. Bougauchi and M. Shibaski, TetLett 1998, 39, 7353.
[4] Rare-Earth Metal Triflates in Organic Synthesis, S. Kobayashi, M. Sugiura, H. Kitagawa and W. W.-L. Lam, Chem. Rev. 2002, 102, 2227–2302. DOI: 10.1021/cr010289i Paper.

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NOTES
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Comments
Re: Yb(OTf)3/BINOL catalysed asymmetric acyl-PS formation of KAB26-20 by Murray Robertson
30th July 2012 @ 02:51
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 @ 03:06
Single crystal x-ray diffraction confirmed the crystals as (R)-BINOL