SYNTHESIS AND CHARACTERIZATION OF A PROTECTED AMINO ALCOHOL CONTAINING ORTHO-CARBORANE

The reaction between the alkyne, N-(5-Benzyloxy-2-pentynyl)phthalimide and decaborane (14) in the presence of dimethyl sulfide resulted in t he isolation of 1-C6H4(CO)(2)NCH2-2-C6H5CH2OCH2CH2-1, 2-C2B10H10 (5), 1-methylphthalimido-2-ethylbenzyl ether-o-carborane, in moderate yield . Compound 5 was characterized by single crystal X-ray diffraction stu dy. Compound 5 crystallizes in the PT space group, a = 10.5328 (5) Ang strom, b = 11.9209 (6) Angstrom, c = 10.3451 (3) Angstrom, alpha = 110 .492 (3)degrees, beta = 102.868 (3)degrees, gamma = 87.279 (2)degrees, Z = 2, D-calc = 1.226 g/cm(3), R = 0.0491 for 3521 reflections with F >4.0 sigma. Deprotection of the ether linkage of 5 results in the form ation of 1-C6H4(CO)(2)NCH2-2-HOCH2CH2-1, 2-C2B10H10 (6), 1-methylphtha limido-2-ethylalcohol-o-carborane. The transformation is accomplished by hydrogenation of (5) over a Pd/C catalyst and resulted in the effic ient conversion of (5) into (6) (83% yield). Experimental details and analytical data leading to the identification of the reported compound s is provided. (C) 1998 Elsevier Science Ltd. All rights reserved.