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Sunday 24 November 2013

(R)-2-(2-hydroxy-1-phenylethyl)isoindoline-1,3-dione


   Reaction Scheme: <img src="/images/empty.gif" alt="" />Protection of phenyl glycinol using <span id="csm1374586974145" class="csm-chemical-name" title="phthalic anhydride">phthalic anhydride</span><img src="/images/empty.gif" alt="" />

Equimolar ratios of both heated at 145 deg c for 4 hrs and then the oil  titurated in DCM , Dried over sodium sulphate , evapn gives oil , used as such for next step. is a method of protection of amino gp

 2-[(1R)-2-Hydroxy-1-phenylethyl]-1H-isoindole-1,3(2H)-dione

ChemSpider 2D Image | 2-[(1R)-2-Hydroxy-1-phenylethyl]-1H-isoindole-1,3(2H)-dione | C16H13NO3205380-30-9  cas no

SpectralData

1H NMR (400 MHz, 298 K, CDCl3) δH 7.83 – 7.74 (2H, m, Pht), 7.70 – 7.60 (2H, m, Pht), 7.49 (2H, d, 3JHH = 7.4 Hz, Ph), 7.41 – 7.23 (3H, m, Ph), 
5.51 (1H, dd, 3JHH = 8.9 Hz, 3JHH = 5.0 Hz, CH), 
4.76 – 4.66 (1H, m, CH2), 
4.24 (1H, dd, 3JHH = 11.4 Hz, 4JHH = 4.9 Hz, CH2), 
3.47 (1H, s, OH).


13C NMR (100 MHz, 298 K, CDCl3) δC 168.89 (C=O), 
136.88, 134.08 (Pht), 131.72, 128.70, 128.13, 127.97 (Ph), 123.31 (Pht), 
61.98 (CH2), 57.46 (CH).

MS (ESI+) m/z 290.1 ([M+Na]+)

IR (cm-1) ν 3457, 1772, 1700, 1611, 1585, 1495, 1467, 1388, 1358, 1332, 1288, 1266, 1185, 1172, 1120, 1065, 1040, 1013, 999, 962, 919, 877, 838, 793, 765, 719, 698.


M. D. Chen, M. Z. He, X. Zhou, L. Q. Huang, Y. P. Ruan and P. Q. Huang, Tetrahedron, 2005, 61, 1335-1344http://dx.doi.org/10.1016/j.tet.2004.10.109
 http://www.sciencedirect.com/science/article/pii/S0040402004019143

Aguilar, Nuria; Moyano, Albert; Pericas, Miquel A.; Riera, Antoni 
Synthesis, 1998 ,  3,   p. 313 - 316

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