2799-16-8

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(-)-1-Amino-2-propanol is used as an intermediate in the synthesis of various pharmaceutical compounds, particularly those with chiral centers. Its unique R-configuration makes it a valuable building block for the development of enantiomerically pure drugs, which can have significant advantages in terms of efficacy and safety.
Used in Chemical Synthesis:
(R)-(-)-1-Amino-2-propanol is used as a chiral auxiliary in asymmetric synthesis, helping to control the stereochemistry of the target molecule. This application is crucial in the production of enantiomerically pure compounds, which are often required for biological activity and to avoid potential side effects associated with the less active enantiomer.
Used in Chiral Solvents:
(R)-(-)-1-Amino-2-propanol can be used as a chiral solvent in various analytical techniques, such as circular dichroism (CD) spectroscopy and nuclear magnetic resonance (NMR) spectroscopy. These techniques rely on the interaction between the chiral solvent and the chiral analyte to provide information about the structure and conformation of the analyte.
Used in Personal Care Industry:
(R)-(-)-1-Amino-2-propanol can be used in the formulation of personal care products, such as cosmetics and toiletries, due to its amphiphilic nature. It can act as a surfactant, emulsifier, or viscosity modifier, improving the texture and stability of the final product.
Used in Environmental Applications:
(R)-(-)-1-Amino-2-propanol can be employed in the development of chiral catalysts for asymmetric reactions, which are essential in the synthesis of environmentally friendly chemicals and materials. These catalysts can help reduce waste, improve reaction efficiency, and minimize the use of hazardous substances in the production process.

InChI:InChI=1/C3H9NO/c1-3(5)2-4/h3,5H,2,4H2,1H3/t3-/m1/s1

Upstream product

• 78-96-6 3-amino-2-propanol 
• 598-81-2 (R)-lactamide 
• 72-19-5 L-threonine 
• 75-56-9 methyloxirane 
• 1187326-76-6 (R)-1-(naphthalen-1-ylmethylamino)propan-2-ol 
• 10017-09-1 (+)-2-hydroxypropionitrile 
• 77463-87-7 N,N'-bis-(2-hydroxy-propyl)-urea 

Downstream Products

• 158151-20-3 (2R)-1-(1H-pyrrol-1-yl)-2-propanol 
• 130793-70-3 (2R)-N-benzyloxycarbonyl-2-hydroxypropylamine 
• 162240-94-0 (R)-1-<(Phenylmethyl)amino>-2-propanol 
• 17435-30-2 (R)-1-(5-Amino-6-chloro-pyrimidin-4-ylamino)-propan-2-ol 
• 635682-96-1 (S)-3,3,3-Trifluoro-N-((R)-2-hydroxy-propyl)-2-methoxy-2-phenyl-propionamide 
• 444607-73-2 (R)-(-)-8-(2,6-difluorophenyl)-4-(4-fluoro-2-methylphenyl)-2-[N-(1-amino-2-propanol)]-8H-pyrido[2,3-d]pyrimidin-7-one 
• 444607-79-8 (R)-(-)-8-(2-fluorophenyl)-4-(4-fluoro-2-methylphenyl)-2-[N-([2-methyl-2-hydroxy]ethylamino)]-8H-pyrido[2,3-d]pyrimidin-7-one 
• 444607-87-8 (R)-(-)-8-cyclohexyl-4-(4-fluoro-2-methylphenyl)-2-[N-1-amino-2-hydroxypropyl]-8H-pyrido[2,3-d]pyrimidin-7-one 
• 817185-87-8 8-[(2,6-dimethylbenzyl)amino]-N-[(2R)-2-hydroxypropyl]-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide 

Relevant academic research and scientific papers

STEREOCHEMISTRY OF THE RING CLOSURE REACTION OF OPTICALLY ACTIVE 1-AMINO-2-PROPANOL

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.

Preparation method of chiral 1-amino-2-propanol

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.

Organocatalytic Decarboxylation of Amino Acids as a Route to Bio-based Amines and Amides

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.

A R - 1 - amino -2 - propanol (by machine translation)

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)

HIV INTEGRASE INHIBITORS

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.

Decarboxylation of a Wide Range of Amino Acids with Electrogenerated Hypobromite

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.

Rearrangement of N-alkyl 1,2-amino alcohols. Synthesis of (S)-toliprolol and (S)-propanolol

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.

Process for preparing amines

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.

One-pot sequence for the decarboxylation of α-amino acids

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.

SUBSTITUTED QUINAZOLINE DERIVATIVES AND THEIR USE AS INHIBITORS

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