- STEREOCHEMISTRY OF THE RING CLOSURE REACTION OF OPTICALLY ACTIVE 1-AMINO-2-PROPANOL
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Optically active 2-methylethylenimine has been prepared via ring closure reaction of (R)- or (S)- 1-amino-2-propanol.The reaction is explained by an intramolecular SN mechanism.
- Yahiro, Nobuhide
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Read Online
- Preparation method of chiral 1-amino-2-propanol
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The invention provides a preparation method of chiral 1-amino-2-propanol, which comprises the following steps: carrying out ring-opening reaction on trifluoroacetamide and chiral epoxypropane to generate an intermediate product I; and carrying out hydrolysis reaction on the intermediate product I to obtain the chiral 1-amino-2-propanol. According to the preparation method, the target product can be obtained through a two-step reaction, so that the preparation process of chiral 1-amino-2-propanol is greatly simplified; and the raw materials trifluoroacetamide and chiral epoxypropane are cheap and easily available, the reaction process is simple, the operation is convenient, harsh reaction conditions such as high temperature and high pressure are not needed, complex purification, post-treatment and chiral resolution operations are also not needed, and the obtained target product has high purity, high yield and high optical activity, and is suitable for large-scale industrial preparation.
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Paragraph 0060-0061; 0065-0069; 0080-0081; 0084-0085
(2020/09/09)
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- Organocatalytic Decarboxylation of Amino Acids as a Route to Bio-based Amines and Amides
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Amino acids obtained by fermentation or recovered from protein waste hydrolysates represent an excellent renewable resource for the production of bio-based chemicals. In an attempt to recycle both carbon and nitrogen, we report here on a chemocatalytic, metal-free approach for decarboxylation of amino acids, thereby providing a direct access to primary amines. In the presence of a carbonyl compound the amino acid is temporarily trapped into a Schiff base, from which the elimination of CO2 may proceed more easily. After evaluating different types of aldehydes and ketones on their activity at low catalyst loadings (≤5 mol%), isophorone was identified as powerful organocatalyst under mild conditions. After optimisation many amino acids with a neutral side chain were converted in 28–99 % yield in 2-propanol at 150 °C. When the reaction is performed in DMF, the amine is susceptible to N-formylation. This consecutive reaction is catalysed by the acidity of the amino acid reactant itself. In this way, many amino acids were efficiently transformed to the corresponding formamides in a one-pot catalytic system.
- Claes, Laurens,Janssen, Michiel,De Vos, Dirk E.
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p. 4297 - 4306
(2019/08/26)
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- A R - 1 - amino -2 - propanol (by machine translation)
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The invention relates to the field of medicine, in particular to a (R)-1 - amino -2 - propanol. In order to (R)- propylene oxide is the raw material of the process for preparing high optical purity of the (R)-1 - amino -2 - propanol, the production process is an alternative to the original using L - threonine reduction to produce the (R)-1 - amino -2 - propanol production process. (R)-1 - amino -2 - propanol is preparation of lymphocyte AIDS drug tynofovir important intermediates, the invention will be (R)- epoxy propane, ammonia with alkone into reactor reaction, the obtained intermediate hydrolysis, concentrated, rectification and purification. Thus, can solve the high price of the raw material, the yield is low, tynofovir cost is increased. The invention obviously reduce the production cost, no waste generation, without environmental pollution, realize green production, the raw material is cheap, simple steps and the cost is low, high purity of the product, is suitable for industrial production. (by machine translation)
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Paragraph 0043-0046
(2017/10/07)
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- HIV INTEGRASE INHIBITORS
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The present invention features compounds that are HIV integrase inhibitors and therefore are useful in the inhibition of HIV replication, the prevention and/or treatment of infection by HIV, and in the treatment of AIDS and/or ARC.
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- Decarboxylation of a Wide Range of Amino Acids with Electrogenerated Hypobromite
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Bromide-assisted electrochemical decarboxylation efficiently produces valuable nitriles in high yields from a wide range of naturally occurring amino acids in a single step. Bromide salts are used as both redox mediators and supporting electrolytes in a simple one-compartment setup. As demonstrated for lysine, the selectivity of the decarboxylation can be tuned towards nitriles, amines or amides. An electrochemical system is developed that allows the selective decarboxylation of a wide range of amino acids. Valuable nitriles are obtained in high yields in a single step by using bromide salts as both redox mediators and supporting electrolytes. The product selectivity of lysine can be tuned towards nitriles, amines, or amides.
- Matthessen, Roman,Claes, Laurens,Fransaer, Jan,Binnemans, Koen,De Vos, Dirk E.
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p. 6649 - 6652
(2016/02/19)
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- Rearrangement of N-alkyl 1,2-amino alcohols. Synthesis of (S)-toliprolol and (S)-propanolol
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N-alkyl 1,2-amino alcohols were rearranged stereospecifically by using TFAA/Et3N. This rearrangement has been used to synthesize N-isopropyl-3-(aryloxy)-2-hydroxypropylamines, β-adrenergic blocking agents such as (S)-toliprolol and (S)-propanolol.
- Duthion, Béranger,Métro, Thomas-Xavier,Gomez Pardo, Domingo,Cossy, Janine
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experimental part
p. 6696 - 6706
(2011/02/26)
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- Process for preparing amines
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A process for preparing an amine which comprises in preparing an amine by decarboxylating an α-amino acid under heating in a high boiling liquid polymer having average molecular weight 200 to 6000, and directly recovering this amine by distillation in the same reaction system, namely in one pot.
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Page/Page column 2
(2008/06/13)
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- One-pot sequence for the decarboxylation of α-amino acids
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Treatment of an α-amino acid with N-bromosuccinimide in water at pH 5 or in an alcoholic-aqueous ammonium chloride mixture, followed by addition of nickel(II) chloride and sodium borohydride, effected an overall decarboxylation via an intermediate nitrile to afford the corresponding amine in good yield.
- Laval, Gilles,Golding, Bernard T.
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p. 542 - 546
(2007/10/03)
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- SUBSTITUTED QUINAZOLINE DERIVATIVES AND THEIR USE AS INHIBITORS
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The use of a compound of formula (I) 1 or a salt, ester or amide thereof; where X is O, or S, S(O) or S(O)2, or NR6 where R6 is hydrogen or C1-6 alkyl,; R5 is an optionally substituted 5-membered heteroaromatic ring, R1, R2 ,R3, R4 are independently selected from various specified moieties, in the preparation of a medicament for use in the inhibition of aurora 2 kinase. Certain compounds are novel and these, together with pharmaceutical compositions containing them are also described and claimed
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- Resolution of β-aminoalcohols and 1,2-diamines using fractional crystallization of diastereomeric salts of dehydroabietic acid
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(S)-(+)-1-Amino-3-phenyloxy-2-propanol, (R)-(-)-2-amino-1-phenylethanol, (S)-(+)-1-amino-2-propanol, (1S,2S)-(+)-2-aminocyclohexanol and (1S,2S)-(+)-1,2-diaminocyclohexane were resolved using dehydroabietic acid. It was shown that good to high enantiomeric purity, between 81～>99% ee, was obtained and that dehydroabietic acid could be easily and efficiently recovered in a reusable form.
- Guangyou, Zhang,Yuquing, Liao,Zhaohui, Wang,Nohira, Hiroyuki,Hirose, Takuji
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p. 3297 - 3300
(2007/10/03)
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- Process for the selective enzymatic hydroxylation of aldehydes and ketones
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A process for the selective enzymatic hydroxylation of aldehydes and ketones using chiral anchor-protective groups.
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- Decarboxylation of α-amino acids containing two and three stereogenic centers: A simple one-step procedure to prepare two optically active β- amino alcohols and a bicyclic pyrrolidine derivative
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The decarboxylation of L-threonine (2S,3R)-1, L-hydroxyproline (2S,4R)-2 and D-2-azabicyclo[3.3.0]octan-3-carboxylic acid (1R,3R,5R)-5 yield in a simple one-step procedure the corresponding optically active β-amino alcohols (R)-3 and (R)-4 and the bicyclic pyrrolidine derivative (1R,5R)-6 in 72-82% yield and >99% ee.
- Wallbaum,Mehler,Martens
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p. 1381 - 1387
(2007/10/02)
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- A practical synthesis of both enantiomers of 1-amino-2-propanol and propylene oxide
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A practical large-scale synthesis of both enantiomers of 1-amino-2-propanol 1 from L- and D-threonine is described. Greater than 99% e.e. propylene oxide 2 is obtained from 1 through a diazotization under basic conditions.
- Rossen,Simpson,Wells
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p. 1071 - 1074
(2007/10/02)
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- A NOVEL DECARBOXYLATION OF α-AMINO ACIDS. A FACILE METHOD OF DECARBOXYLATION BY THE USE OF 2-CYCLOHEXEN-1-ONE AS A CATALYST
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In the presence of a catalytic amount of 2-cyclohexen-1-one, decarboxylation of α-amino acids proceeds smoothly and affords the corresponding amino compounds in good yields.Optically active amino compounds, (3R)-(-)-3-hydroxypyrrolidine and (2R)-(-)-2-hydroxypropylamine are obtained in 93percent and 80percent yields, respectively.
- Hashimoto, Mitsunori,Eda, Yutaka,Osanai, Yasutomo,Iwai, Toshiaki,Aoki, Seiichi
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p. 893 - 896
(2007/10/02)
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- Ligand Exchange Chromatography of Amino Alcohols. Use of Schiff Bases in Enantiomer Resolution
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A new method for enantiomeric resolution of primary amino alcohols by HPLC is described involving derivatization to the salicylaldehyde Schiff base followed by ligand exchange chromatography (LEC) with chiral L-proline-bonded stationary phases.All of the α-amino alcohols with a hydroxyl substituent on the asymmetric carbon examined were resolved, including catecholamines and other β-hydroxyphenethylamines.The copper(II) ion employed in LEC serves to stabilize the Schiff base, whereas the derivative permits complexation in a manner favorable for resolution and enhanced detection.A possible structure for the mixed complex responsible for separation is suggested.From this structure, a correlation between elution order and configuration is proposed.
- Gelber, Loren R.,Karger, Barry L.,Neumeyer, John L.,Feibush, Binyamin
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p. 7729 - 7734
(2007/10/02)
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