- PYRROLO-PYRROLE CARBAMATE AND RELATED ORGANIC COMPOUNDS, PHARMACEUTICAL COMPOSITIONS, AND MEDICAL USES THEREOF
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The invention provides pyrrolo-pyrrole carbamate and related organic compounds, compositions containing such compounds, medical kits, and methods for using such compounds and compositions to treat medical disorders, e.g., solid tumor cancer, obesity, Down's syndrome, Alzheimer's disease, or pain, in a patient. The octahydropyrrolo pyrrole carbamates could be derived from hexafluoroisopropanol, Ν,Ν-disuccinimide and such. The activity of carbamates in MAGL, FAAH, and ABHD6 assays are also described.
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Paragraph 00550; 00551
(2015/01/16)
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- Versatile iridicycle catalysts for highly efficient and chemoselective transfer hydrogenation of carbonyl compounds in water
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Cyclometalated iridium complexes are shown to be highly efficient and chemoselective catalysts for the transfer hydrogenation of a wide range of carbonyl groups with formic acid in water. Examples include α-substituted ketones (α-ether, α-halo, α-hydroxy, α-amino, α-nitrile or α-ester), α-keto esters, β-keto esters and α,β-unsaturated aldehydes. The reduction was carried out at substrate/catalyst ratios of up to 50000 at pH 4.5 and required no organic solvent. The protocol provides a practical, easy and efficient way for the synthesis of β-functionalised secondary alcohols, such as β-hydroxyethers, β-hydroxyamines and β-hydroxyhalo compounds, which are valuable intermediates in pharmaceutical, fine chemical, perfume and agrochemical synthesis. Water wonder: Iridicycle catalysts are versatile and allow the highly efficient and chemoselective transfer hydrogenation of a variety of carbonyl compounds, including problematic and challenging ones, with formate in neat water (see scheme).
- Talwar, Dinesh,Wu, Xiaofeng,Saidi, Ourida,Salguero, Noemí Poyatos,Xiao, Jianliang
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supporting information
p. 12835 - 12842
(2015/03/30)
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- Asymmetric organozincate additions to ethyl 2,2,2-trifluoropyruvate
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A chromatography-free synthesis of enantiomerically enriched chiral α-trifluoromethyl α-hydroxy acids prepared via an asymmetric (R)-BINOL-mediated organozincate addition to ethyl 2,2,2-trifluoropyruvate (1) is reported. Georg Thieme Verlag Stuttgart.
- Gosselin, Francis,Britton, Robert A.,Mowat, Jeffrey,O'Shea, Paul D.,Davies, Ian W.
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p. 2193 - 2196
(2008/02/10)
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- Process for producing 3,3,3-trifluoro-2-hydroxypropionic acid or its derivative
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The invention relates to a process for producing 3,3,3-trifluoro-2-hydroxypropionic acid. This process includes the step of (a) bringing a 1,1-dihalogeno-3,3,3-trifluoroacetone into contact with a basic aqueous solution. The obtained 3,3,3-trifluoro-2-hydroxypropionic acid may be reacted with a C1-C6 lower alcohol under an acidic condition, thereby producing a 3,3,3-trifluoro-2-hydroxypropionate. This propionate may be reacted with a hydride reducing agent (e.g., sodium borohydride), thereby producing 3,3,3-trifluoro-2-hydroxypropanol. These products (i.e., 3,3,3-trifluoro-2-hydroxypropionic acid and its derivatives) are important intermediates for medicines and liquid crystals.
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- An efficient protocol for the reduction of ketones with tin(II) complexes and PMHS
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A mixture of tin(II) triflate/pybox and polymethylhydrosiloxane (PMHS) in methanol effects the efficient reduction of ketones; the use of an enantiomerically pure pybox ligand leads to moderate enantioselectivity. (C) 2000 Elsevier Science Ltd.
- Lawrence, Nicholas J.,Bushell, Simon M.
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p. 4507 - 4512
(2007/10/03)
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- Simple Access to (R)- and (S)-3,3,3-Trifluorolactic Acid and to (R)- and (S)-(Trifluoromethyl)oxirane
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Ethyl trifluoropyruvate (from hexafluoropropylene oxide) is reduced by NaBH4 to rac-trifluorolactic acid which is resolved on a 100-g scale by salt formation with (R,R)- and (S,S)-2-amino-1-phenyl-1,3-propanediol (readily available intermediates of industrial chloroamphenicol synthesis).The enantiomerically pure trifluorolactic acids (>99percent ee by GC analysis on cyclodextrin columns) are converted into (R)- and (S)-(trifluoromethyl)oxirane in an overall yield of 73percent by the following steps: esterification, THP protection of the OH group, LAH reduction and mesylation to the 2-THP-protected mesylate of 3,3,3-trifluoro-1,2-propanediol, and one-pot deprotection (Dowex 50) and cyclization (NaOCH2CH2OH) in ethylene glycol.The enantiomeric purity of the oxirane (b.p. 39 deg C, isolated on a 10-g scale) was determined by GC to be >99percent.Possible synthetic targets are mentioned which should be accessible in enantiomerically pure form from the (trifluoromethyl)oxirane described here. Key Words: Resolution by crystallization of diastereomeric salts / Perfluoropropylene oxide / Trifluoropyruvate / Capillary GC determination of ratios of enantiomers / Cyclodextrine-derived GC columns / Determination of the sense of chirality by chemical correlation / pKs of 3,3,3-trifluoro-2-hydroxypropanoic and 4,4,4-trifluoro-3-hydroxybutanoic acid
- Bussche-Huennefeld, Christoph von .,Cescato, Claudio,Seebach, Dieter
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p. 2795 - 2802
(2007/10/02)
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- REACTION OF HYDROXY AND CARBONYL COMPOUNDS WITH SULFUR TETRAFLUORIDE. XII. REACTIONS OF ESTERS OF ALIPHATIC α- AND β-HYDROXY CARBOXYLIC ACIDS WITH SULFUR TETRAFLUORIDE
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The esters of aliphatic and α- and β-hydroxy carboxylic acids react with sulfur tetrafluoride to form the corresponding esters of fluoro carboxylic acids and alkoxycarbonylalkyl fluorosulfites.If electron-withdrawing substituents are introduced at the α position to the carbon atom attached to the hydroxyl group, the reactions of the esters of hydroxy acids with sulfur tetrafluoride take place with substitution of the carbonyl oxygen by two fluorine atoms.
- Motnyak, L. A.,Burmakov, A. I.,Kunshenko, B. V.,Neizvestnaya, T. A.,Alekseeva, L. A.,Yagupol'skii, L. M.
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p. 1063 - 1074
(2007/10/02)
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