33809-96-0Relevant articles and documents
Catalytic asymmetric cross-couplings of racemic α-bromoketones with arylzinc reagents
Lundin, Pamela M.,Esquivias, Jorge,Fu, Gregory C.
supporting information; experimental part, p. 154 - 156 (2009/04/07)
(Chemical Equation Presented) Nickel box: The first catalytic asymmetric method for cross-coupling arylzinc reagents with α-bromoketones has been developed (see scheme). This stereoconvergent carbon-carbon bond-forming process occurs under unusually mild conditions and without activators, thereby allowing the generation of potentially labile tertiary stereocenters.
Synthesis and Anti-tetrabenazine Activity of C-3 Analogues of Dimethyl-2-phenylmorpholines
Boswell, G. Evan,Musso, David L.,Kelley, James L.,Soroko, Francis E.,Cooper, Barret R.
, p. 33 - 40 (2007/10/03)
A series of analogues of 2-phenylmorpholines with alkyl substituents at the C-3 position were synthesized for anti-tetrabenazine (anti-TBZ) testing in mice.The target compounds were prepared by reaction of (2-bromoalkyl) phenyl ketones 21a-h with the appropriate aminoalcohol 20a-b to form morpholinols 22a-h.Hydride reduction of the morpholinols gave aminodiols 23a-h which were cyclized to morpholines 6, 8, 10-12, 14-16, 18 and 19 by acid catalysis.Compounds 7, 9, 13 and 17 were prepared by reductive formylation.The smaller straight chain substituents of 6, 8, 12 and 15, and the beta branching of the iso-butyl group of 16 were well tolerated; anti-tetrabenazine ED50's were comparable to compounds 2-5.The α-branched, N-methylated, and side chain aryl derivatives were less active.