3198-15-0

Usage

InChI:InChI=1/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3

Upstream product

• 104713-12-4 (1S)-1-phenylprop-2-en-1-ol 
• 917-54-4 methyllithium 
• 154-41-6 erythro-1-phenyl-1-hydroxy-2-propylammonium chloride 
• 133735-62-3 (R)-1-Methyl-2-phenyl-2-((1R,2R,4S,6R,7R)-1,10,10-trimethyl-3-oxa-tricyclo[5.2.1.0^2,6]dec-4-yloxy)-ethylamine 
• 532-28-5 (RS)-mandelonitrile 
• 133812-91-6 <2S-(2a(S*),3aα,4β,7β,7aα)>-α-<(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>benzolacetonitril 
• 492-41-1 (1R,2S)-norephedrine 
• 124368-83-8 (1R,2S)-(-)-2-Amino-1-phenyl-1-<(tert-butyldimethylsilyl)oxy>-propane 
• 154-41-6 norephedrine hydrochloride 
• 104-54-1 3-Phenylpropenol 
• 119-51-7 1-phenyl-1,2-propanedione 2-oxime 
• 93-55-0 1-phenyl-propan-1-one 
• 55253-39-9 (R)-1-hydroxy-1-phenylpropan-2-one oxime 
• 26251-08-1 2-nitro-1-phenylpropan-1-ol 

Downstream Products

• 40058-14-8 (2R,3S,7S,8R)-3,4,8-Trimethyl-2,7-diphenyl-1,6-dioxa-4,9-diaza-5λ⁵-phospha-spiro[4.4]nonane 
• 40058-14-8 (2R,3S,7S,8R)-3,4,8-Trimethyl-2,7-diphenyl-1,6-dioxa-4,9-diaza-5λ⁵-phospha-spiro[4.4]nonane 
• 41234-90-6 (2R,3S,7R,8S)-3,8-Dimethyl-2,7-diphenyl-1,6-dioxa-4,9-diaza-5λ⁵-phospha-spiro[4.4]nonane 
• 41234-90-6 (2R,3S,7R,8S)-3,8-Dimethyl-2,7-diphenyl-1,6-dioxa-4,9-diaza-5λ⁵-phospha-spiro[4.4]nonane 

Relevant academic research and scientific papers

Ueber die Enantiomerentrennung durch Vertilung zwischen fluessigen Phasen

Separation of Enantiomers by Partition between Liquid Phases; Salts of enantiomeric α-aminoalcohols, such as norephedrin, with lipophilic anions, such as hexafluorophosphate ion, can be separated by partition between aqueous and lipophilic phase containing esters of tartaric acid.

NOVEL PROCESS FOR THE PREPARATION OF R-PHENYLACETYLCARBINOL AND β-AMINOALCOHOLS

Disclosed herein is a process for the manufacture of (R)-phenylacetylcarbinol ((R)-PAC), (1R,2S). Ephedrine and its salts, (1R,2S)-norephedrine and its salts and 1-(Phenyl/Substituted phenyl)-2-(amino/alkylamino/dialklyamino) propan-1-ol and its salts, by enzymatic reduction of α-isonitrosopropiophenone (INP) and substituted α-isonitrosopropiophenone (substituted INP). The β-amino alcohols, produced by the process of present invention gives their corresponding diastereomers on Walden inversion. The present preparation process of (R)-PAC with (R)-PAC oxime as an intermediate has the advantage, that propiophenone as a key raw material which is easily available and has a low-price, operationally simple with high yield and a single process leading to the synthesis of several 1,2-aminoalcohol/ β- aminoalcohols active pharmaceutical ingredients. The design approach of the process is to reduce environmental impact of the product by comparing to the present manufacturing process.

A short enantioselective synthesis of ephedrine, amphetamine and their analogues via two stereocentered Co(III)-catalyzed hydrolytic kinetic resolution of racemic syn-benzyloxy epoxide

An efficient route for the synthesis of 6 drugs belonging to phenethylamine and amphetamine classes in excellent overall yields and high optical purity has been described. The strategy involves introduction of stereogenic centers by means of two-stereocentered Co(III)-catalyzed hydrolytic kinetic resolution (HKR) of racemic syn-benzyloxy epoxide followed by Pd-catalyzed regioselective cationic hydrogenation of amino alcohols as the key reactions.

A NOVEL METHOD FOR SYNTHESIS OF OPTICALLY PURE BETA-AMINO ALCOHOLS

A method for the preparation of β-amino alcohol of formula (III) in which R1 is Ph, (substituted) Ph, R2 is C1-8 alkyl or C4-6 cyclo alkyl, R3 = R4R5CHNH2 where, R4 = H, C1-8 alkyl, C4-6 cyclo alkyl, or - COOR6 (R6=C1-C8 alkyl); R5 = (subst) aryl], the method including subjecting an α-hydroxy ketone of formula (I) in which R1 and R2 are as defined above is reacted with a chiral amine of formula R3NH2 where R3 = R4R5CH- where, R4 = H, C1-8 alkyl, C4-6 cycloalkyl, or - COOR6 (R6=C1-8 alkyl), R5 = (subst) aryl] to produce a compound of formula (II) in which R1, R2 and R3 are as defined above, followed by reduction to form the compound of formula (III).

Simple preparation process of syn phenylpropanolamines from racemic O-TBDPS cyanohydrins

In this article, a practically interesting route for the diastereoselective synthesis of phenylpropanolamines has been demonstrated for the first time. Using racemic O-tert-butyldiphenylsilyl (TBDPS) cyanohydrins as the starting materials, various syn phenylpropanolamines and derivatives (e.g., norpseudophedrine) have been successfully prepared in exellent diastereoselectivity via a practically interesting process.

Development of new HPLC chiral stationary phases based on native and derivatized cyclofructans

An unusual class of chiral selectors, cyclofructans, is introduced for the first time as bonded chiral stationary phases. Compared to native cyclofructans (CFs), which have rather limited capabilities as chiral selectors, aliphatic-and aromatic-functionalized CF6s possess unique and very different enantiomeric selectivities. Indeed, they are shown to separate a very broad range of racemic compounds. In particular, aliphatic-derivatized CF6s with a low substitution degree baseline separate all tested chiral primary amines. It appears that partial derivatization on the CF6 molecule disrupts the molecular internal hydrogen bonding, thereby making the core of the molecule more accessible. In contrast, highly aromaticfunctionalized CF6 stationary phases lose most of the enantioselective capabilities toward primary amines, however they gain broad selectivity for most other types of analytes. This class of stationary phases also demonstrates high "loadability" and therefore has great potential for preparative separations. The variations in enantiomeric selectivity often can be correlated with distinct structural features of the selector. The separations occur predominantly in the presence of organic solvents.

CATALYTIC HYDROGENATION PROCESS AND NOVEL CATALYST FOR IT

The present invention provides a novel hydrogenation catalyst, process of preparing the catalyst and process for the preparation of optically active L-norephedrine, [(1R,2S)-2-amino-1-phenyl-1-propanol] by a catalytic hydrogenation process, said catalyst comprising of finely divided nickel metal containing a metal from group III A of the periodic table as an activator and a metal from group VI B or VIII as promoter,

PROCESS FOR PRODUCING OPTICALLY ACTIVE s-AMINO ALCOHOL

A process for easily producing an optically active β-amino alcohol useful as a pharmaceutical intermediate from an inexpensive, readily available starting material is provided. A readily available α-substituted ketone is reacted with an optically active amine to yield a diastereomer mixture of an optically active α-substituted aminoketone. One of the diastereomers is isolated optionally after the diastereomers are converted to salts with an acid. The optically active α-substituted aminoketone or a salt thereof thus isolated was stereoselectively reduced to yield an optically active β-substituted amino alcohol. The optically active β-substituted amino alcohol is subjected to hydrogenolysis to produce an optically active β-amino alcohol or a salt thereof.

PROCESS FOR PREPARATION OF OPTICALLY ACTIVE 1-ERYTHRO-2-AMINO-1-PHENYL-1-PROPANOL

An efficient cost-effective process for preparation of l-erythro-2-amino-1-phenyl-1-propanol from l-1-phenyl-1-hydroxy-2-propanone, which comprises converting l-1-phenyl-1-hydroxy-2-propanone to l-1-phenyl-1-hydroxy-2-propanone oxime and reducing the oxime with a catalyst consisting of finely divided nickel and aluminium metals giving good diastereomeric purity and yield.

Method of preparing optically active alcohols which consist substantially or entirely of one enantiomer

The invention relates to a method of preparing optically active alcohols which consist substantially (at least 75% e.e.) or entirely of one enantiomer of formula 4 STR1 wherein R and A are as defined therein. The method comprises, which maintaining enantiomeric excess, converting an optically active cyanohydrin of formula 1 STR2 into optically active protected cyanohydrin of formula 2 STR3 converting the protected cyanohydrin of formula 2 into an optically active compound of formula 3 STR4 removing the protecting group B.