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18th July 2012 @ 09:02
START: 18/07/12
FINISH: 20/07/12

Scheme%20KAB26-12.png
Table%20KAB26-13.png

Hazard and Risk Assessment
Hazard and Risk Assessment KAB26-4


Previous Experiments
Preparation of MNR42-1
Yb(OTf)3 catalysed acyl-PS to give 1-(6,7-dimethoxy-1-(4-nitrophenyl)-3,4-dihydroisoquinolin-2(1H)-yl)ethanone (KAB26-11)
Yb(OTf)3 catalysed (5 mol%) acyl-PS to give 1-(6,7-dimethoxy-1-(4-nitrophenyl)-3,4-dihydroisoquinolin-2(1H)-yl)ethanone (KAB26-12)

Chemical Information
2-(3,4-dimethoxyphenyl)-N-(4-nitrobenzylidene)ethanamine (KAB23-2) - 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 (KAB26-11) - 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.

Procedure
All acetonitrile was dried over 3 Å molecular sieves (2.5-5 mm) for >24 h

Catalyst Solution Preparation
Yb(OTf)3 (41 mg, 0.063 mmol) was dissolved in acetonitrile (10 mL) to give a 6.4 mM solution.

To 3 Å MS was added acetonitrile (25 mL) and MNR42-1 (199 mg, 0.633 mmol, 1 equiv.). The mixture was cooled in an acetone ice bath. Acetyl chloride (0.05 mL, 0.6 mmol, 1 equiv.), 2,6-lutidine (0.07 mL, 0.06 mmol, 1 equiv.) and the Yb(OTf)3/MeCN solution (5 mL, 0.05 equiv.) were added. The reaction mixture was allowed to warm to ambient temperature and stirred under argon from 19:00.
Off at 15:00, 19/07/12, 20 h. Workup identical to KAB26-12. Crude KAB26-13 (198 mg, 87%)
Column chromatography (65%, EtOAc/hexane, v/v).
Final yield (163 mg, 72%).
Summary and Conclusion

References
[1] S. W. Youn, J. Org. Chem. 2006, 71, 2521-2523. DOI: 10.1021/jo0524775. Paper
[2] K. Manabe, D. Nobutou, S. Kobayashi, Bioorg. Med. Chem. 2005, 13, 5154-5158.
[3] D. Bradley, G. Williams and M. Lawton, J. Org. Chem. 2010, 75, 8351. DOI: 10.1021/jo101589h Paper.

Abbreviations Used:
EtOAc = ethyl acetate
TLC = thin layer chromatography
RM = reaction mixture
MS = molecular sieves
Soln = solution


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NOTES
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Linked Posts
Attached Files
Table KAB26-13