Quality Control of (S)-1-(Dimethylamino)propan-2-ol. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: (S)-1-(Dimethylamino)propan-2-ol, is researched, Molecular C5H13NO, CAS is 53636-17-2, about Fluoride ion-catalyzed reduction of aldehydes and ketones with hydrosilanes. Synthetic and mechanistic aspects and an application to the threo-directed reduction of α-substituted alkanones. Author is Fujita, Makoto; Hiyama, Tamejiro.
Reduction of aldehydes and ketones with hydrosilanes proceeded in the presence of a catalytic amount of Bu4NF or tris(diethylamino)sulfonium difluorotrimethylsilicate in aprotic polar solvents under mild conditions. A significant isotope effect (kH/kD = 1.50) was observed in competitive reduction of acetophenone with HSiMe2Ph and DSiMe2Ph. The reaction was first order in the concentration of HMPA. Reduction of 2-methylcyclohexanone gave cis-2-methylcyclohexanol with selectivities up to 95%. The kinetic and stereochem. results suggest that a hexavalent fluorosilicate [HSiR3F(HMPA)]- is involved. α-Alkoxy (acyloxy or dimethylamino) ketones were transformed to threo alcs. in high diastereoselectivities. The reduction was also applied to α-methyl-β-oxo amides, RCOCHMeCONR12, to afford the corresponding threo alcs. in >98% selectivity. The threo selectivity is explained in terms of the Felkin-Anh model in which interaction of carbonyl oxygen with a countercation is ideally suppressed. The threo-directed reduction was applied to (R)-1-phenyl-4-(2-tetrahydropyranyloxy)-1-penten-3-one and N-(2-benzoylpropanoyl)piperidine. The resulting threo alcs. were resp. converted into (2R,3S)-2,3-(cyclohexylidenedioxy)butanal, a key intermediate of daunosamine synthesis, and into a pharmacol. useful compound, threo-N-(3-hydroxy-2-methyl-3-phenylpropyl)piperidine.
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Reference:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics