- Preparation method of piperidine alcohol compound
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Discloses a preparation method of a piperidinol compound, wherein the piperidinol is selected from (R)-1 - benzyl -3 - piperidinol. 1 -benzyl -3 - piperidone as reaction raw material and application thereof LiAlH4 A chiral reagent formed by the
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Paragraph 0024-0036
(2021/10/05)
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- Stereo-complementary bioreduction of saturated N-heterocyclic ketones
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The asymmetric bioreduction of several saturated N-heterocyclic ketones is demonstrated in a stereo-complementary fashion using the ketoreductases READH and ChKRED20 for the production of (S)- and (R)-alcohols, respectively. The reaction accepts substrates with a five-, six- or seven-membered ring, and exhibits excellent stereoselectivity when using 2-propanol as both the ultimate reducing agent and cosolvent, achieve >99% ee in the majority of cases for both enantiomers.
- Li, Chao,Liu, Yan,Pei, Xiao-Qiong,Wu, Zhong-Liu
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- Chiral-1-tert-butoxy-carbonyl-3-hydroxy-piperidine, and the preparation of chiral turning method
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The invention relates to preparation of chirality-1-t-butyloxycarboryl-3-hydroxy piperidine and a method for chirality turning. The preparation mainly comprises the following steps: resolving N-benzyl-3-hydroxy piperidine as a raw material to obtain a (S) or (R)-1-benzyl-3-hydroxy piperidine camphorsulfonic acid salt, performing alkali freedom to obtain (S) or (R)-1-benzyl-3-hydroxy piperidine, performing palladium carbon hydrogenation debenzylation/t-butyloxycarboryl protection to obtain (S) or (R)-1-t-butyloxycarboryl-3-hydroxy piperidine, acylating substituting sulfonyl chloride of (R) or (S)-1-substituting-3-hydroxy piperidine as a raw material to obtain (R) or (S)-1-substituting-3-hydroxy piperidine sulfonate, substituting by using substituting carboxylate to obtain (S) or (R)-1-substituting-3-hydroxy piperidine carboxylic ester, and performing alkaline hydrolysis to obtain (S) or (R)-1-substituting-3-hydroxy piperidine. The synthesis route is gentle in reaction condition, and is applicable to industrial large-scale production.
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Paragraph 0054; 0060; 0091
(2016/12/01)
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- NOVEL COMPOUNDS AS ANTI-TUBERCULAR AGENTS
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The present invention relates to novel compounds of formula (1): The present invention also discloses compounds of formula (1) along with other pharmaceutical acceptable excipients and use of the compounds as anti-tubercular agents.
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Page/Page column 40
(2015/12/17)
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- Preparation of enantiomerically pure N-heterocyclic amino alcohols by enzymatic kinetic resolution
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Abstract The synthesis of both enantiomers of N-benzyl-3-hydroxypyrrolidine and N-benzyl-3-hydroxypiperidine via enzymatic kinetic resolution of the corresponding racemic esters is described. Various commercially available hydrolases were studied as biocatalysts in native and immobilized form. The best results were obtained with lipases PS, AK, CAL-B and with protease Alcalase, which were active and selective for the kinetic resolutions of racemic esters (E > 100). Under optimized reaction conditions, highly enantiomerically enriched (up to 99.5% ee) resolution products were obtained. Lipase and protease showed opposite enantiopreference on the esters, allowing the preparation of both enantiomers of the target compounds. Semi-continuous reactions in column reactors with immobilized biocatalysts were also performed with high enantioselectivities. Inversion of the configuration at C(3) of N-benzyl-3-hydroxypyrrolidine was quantitatively effected in a short number of steps.
- Tofani, Giorgio,Petri, Antonella,Piccolo, Oreste
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p. 638 - 643
(2015/08/03)
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- An efficient dynamic kinetic resolution of N-heterocyclic 1,2-amino alcohols
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A chemoenzymatic dynamic kinetic resolution (DKR) of N-heterocyclic amino alcohols is described. Various lipases were studied as biocatalysts for the kinetic resolution of N-heterocyclic 1,2-amino alcohols. The influence of the support of the enzymes on t
- Lihammar, Richard,Millet, Renaud,Baeckvall, Jan-E.
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supporting information; scheme or table
p. 2321 - 2327
(2011/10/19)
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- Simple one-pot process for the bioresolution of tertiary amino ester protic ionic liquids using subtilisin
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An efficient hydrolase-catalyzed bioresolution of tertiary amino ester protic ionic liquids has been demonstrated. Protic ionic liquids have been prepared in one step from the corresponding tertiary amino alcohols by treatment with butyric anhydride. Afte
- Brossat, Maude,Moody, Thomas S.,Taylor, Stephen J.C.,Wiffen, Jonathan W.
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experimental part
p. 2112 - 2116
(2010/02/28)
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- Stereospecific rearrangement of β-amino alcohols catalyzed by H 2SO4
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Highly enantioselective rearrangement of β-amino alcohols was realized by using a catalytic amount of H2SO4. Georg Thieme Verlag Stuttgart.
- Métro, Thomas-Xavier,Pardo, Domingo Gomez,Cossy, Janine
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p. 2888 - 2890
(2008/02/12)
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- Highly enantioselective synthesis of β-amino alcohols: A catalytic version
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(Chemical Equation Presented) Highly enantioselective rearrangement of β-amino alcohols was realized by using a catalytic amount of trifluoroacetic anhydride.
- Metro, Thomas-Xavier,Pardo, Domingo Gomez,Cossy, Janine
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p. 6556 - 6561
(2008/02/10)
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- Synthesis, 18F-labeling, and biological evaluation of piperidyl and pyrrolidyl benzilates as in vivo ligands for muscarinic acetylcholine receptors
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A series of 31 compounds based on the piperidyl or pyrrolidyl benzilate scaffold were prepared from methyl benzilate and 4-piperidinol, (R)-(+)-3-piperidinol, or (R)-(+)-3-pyrrolidinol. Amine substituents included alkyl and aralkyl groups. In vitro Ki values ranged from 0.05 nM to >100 nM. (R)-N-(2-Fluoroethyl)-3-piperidyl benzilate (3-FEPB, 22, Ki = 12.1 nM) and N-(2-fluoroethyl)-4-piperidyl benzilate (4-FEPB, 8, Ki = 1.83 nM) were selected for radiolabeling with fluorine-18. Using alkylation with 2-[18F]fluoroethyl triflate, 3-[18F]FEPB (42) and 4-[18F]-FEPB (43) were produced in 7-9% radiochemical yield and >97% radiochemical purity. For in vivo studies, retention was moderate in mouse brain for 42; however, blocking with scopolamine showed that uptake was not muscarinic cholinergic receptor-mediated. Conversely, 43 exhibited high, receptor-mediated retention in mouse brain, with significant clearance after 1 h. These results suggest that 43 could have applications as an in vivo probe for measuring endogenous acetylcholine levels.
- Skaddan,Kilbourn,Snyder,Sherman,Desmond,Frey
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p. 4552 - 4562
(2007/10/03)
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- Ring expansion - Formation of optically active 3-hydroxypiperidines from pyrrolidinemethanol derivatives
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Treatment of pyrrolidinemethanol derivatives (-)-1, (-)-6, (-)7, 8, (- )-9, (+)-10, (-)-11, and (-)-21 with trifluoroacetic anhydride and then with Et3N afforded, after hydrolysis of the trifluoroacetyl group with NaOH, the optically active -hy
- Cossy, Janine,Dumas, Cecile,Gomez Pardo, Domingo
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p. 1693 - 1699
(2007/10/03)
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- Lipase-catalyzed practical synthesis of (R)-1-benzyl-3-hydroxy-2,5-pyrrolidinedione and its related compounds
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A practical method for preparing (R)-1-benzyl-3-hydroxy-2,5-pyrrolidinedione (1) was investigated by the use of the enzymatic hydrolysis of its acetate (2a). Among several hydrolases examined here, lipase PS from Pseudomonas cepacia gave the best result: In a mixed solvent (1:1 v/v) of dioxane and a phosphate buffer (pH 7), the hydrolysis took place smoothly with a high enantioselectivity (E > 3000). Several 3-alkanoyl derivatives of 1 were subjected to the lipase PS-catalyzed hydrolysis. The chain length of the alkanoyl does not noticeably influence the reaction rate or the enantioselectivity. In contrast, the hydrolysis of the 1-benzoyl derivative proceeded slowly with a low enantioselectivity (E = 19). The syntheses of optically active 3-hydroxypyrrolidines and 3-hydroxypiperidines were also achieved under the reaction conditions similar to the lipase PS-catalyzed hydrolysis of 2a.
- Tomori, Hiroshi,Shibutani, Kuniko,Ogura, Katsuyuki
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p. 207 - 215
(2007/10/03)
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- Formation of Optically Active 3-Hydroxypiperidines
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The synthesis of enantiomerically pure 3-hydroxypiperidines has been achieved from prolinol.
- Cossy, Janine,Dumas, Cecile,Michel, Patrick,Pardo, Domingo Gomez
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p. 549 - 552
(2007/10/02)
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- Synthesis and pharmacological activity of stereoisomers of 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid methyl 1-(phenylmethyl)-3-piperidinyl ester
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1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid methyl 1-(phenylmethyl)-3-piperidinyl ester 1, a highly potent calcium antagonist, was separated into stereo- and optical isomers to investigate the differences of antihypertensive activities between them. Fractional crystallization of the hydrochlorides of 1 gave α- and β-diasterioisomers. The α-isomer (benidipine hydrochloride, KW-3049) showed very strong hypotensive effect, but little activity was observed in the β-isomer. From optically resolved 1,4-dihydro-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-3-pyridi necarboxylic acids 2, and 1-benzyl-3-piperidinols 3, four optical isomers of 1 were synthesized, and their absolute configurations were deduced. The hypotensive activity of (+)-α, namely (S)-(S)-1, was 30 to 100 times stronger than that of (-)-α in intravenously administered spontaneously hypertensive rats.
- Muto,Kuroda,Kawato,Karasawa,Kubo,Nakamizo
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p. 1662 - 1665
(2007/10/02)
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