STRUCTURE OF A CHIRAL BICYCLIC BETA-HYDROXYPHOSPHONAMIDE - A PRODUCT OF KINETIC RESOLUTION IN AN OLEFINATION REACTION, C22H35N2O2P

C22H35N2O2P, M(r) = 390.51, monoclinic, P2(1), a = 9.101 (3), b = 8.612 (6), c = 13.790 (5) angstrom, beta = 92.29 (3)-degrees, V = 1080.0 (9) angstrom3, Z = 2, D(x) = 1.201 Mg m-3, lambda(Mo K-alphaBAR) = 0.71069 angstrom, mu = 0.14 mm-1, T = 293 K, R = 0.044, wR = 0.031 for 1355 observed reflections. The title compound, (3aR,7aR)-2-{(R)-alpha-[(1R,2S)-1-hydroxy-2-methyl-cyclohexyl]phenylmethyl}-1,3-dimethyl-2,3,3a,4,5,6,-7,7a-octahydro-1H-1,3,2-lambda-5-benzodiazaphosphole 2-oxide, is constituted of a (1R,2R)-NN'-dimethyl-1,2-diaminocyclohexane group attached to a tetrahedrally coordinated phosphoryl group. A phenylmethyl group with the R configuration bridges the phosphorus atom and a (IR,2S)-1-hydroxy-2-methylcyclohexyl group. The tertiary alcohol is in the axial position and the 2-methyl group is in the equatorial position. An intramolecular hydrogen bond occurs between the phosphoryl group and the hydroxyl group which restricts the conformation. The molecules are held in the crystal by van der Waals interactions.