90-85-7

Usage

Properties

1. Molecular formula: C20H23NO
2. Derivative of benzyl alcohol
3. Contains a benzene ring
4. Contains an aminoethyl group
5. Contains a methylbenzylamino group
6. Used in pharmaceutical and medicinal applications
7. Used in synthesis of other organic compounds
8. Potential uses in research and development

Specific content

alpha-[1-(methylbenzylamino)ethyl]benzyl alcohol is a chemical compound
Contains a benzene ring, an aminoethyl group, and a methylbenzylamino group
Versatile chemical with potential applications in various industries
May be used in the study of organic chemistry and drug design.

Upstream product

• 621-08-9 Dibenzyl sulfoxide 
• 299-42-3 (R,R)-(-)-pseudoephedrine 
• 90-85-7 (+/-)-erythro-2-(methyl-benzyl-amino)-1-phenyl-propanol-⁽¹⁾ 
• 299-42-3 ephedrine 
• 100-44-7 benzyl chloride 
• 61347-76-0 NH-benzyl-(1R,2S)-norephedrine 
• 77-78-1 dimethyl sulfate 
• 100-39-0 benzyl bromide 
• 258827-43-9 (2rac,4S,5R)-3,4-dimethyl-2,5-diphenyl-1,3-oxazolidine 
• 50-00-0 formaldehyd 
• 64-18-6 formic acid 
• 100-52-7 benzaldehyde 
• 16735-30-1 2-(N-benzyl-N-methylamino)-1-phenylpropan-1-one 
• 90-82-4 rac-pseudoephedrine 

Downstream Products

• 573701-36-7 2-Diazo-3-oxo-butyric acid (1R,2S)-2-(benzyl-methyl-amino)-1-phenyl-propyl ester 
• 774596-70-2 (3S,4R)-N⁽²⁾,3-dimethyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 1255530-21-2 C₂₁H₂₅NO₂ 
• 159099-80-6 (1S,2S)-2-(N-benzyl-N-methylamino)-1-phenyl-1-propanol 
• 88762-93-0 (1S,2R)-N-benzylephedrine 
• 90-85-7 (1R,2S)-1-phenyl-2-(N-methyl-N-benzylamino)propan-1-ol 

Relevant academic research and scientific papers

A dimethylzinc/diphenylphosphinoylimine approach to the asymmetric synthesis of the calcimimetic agent NPS R-568

An asymmetric synthesis of the calcimimetic agent NPS R-568 using a (1R,2S)-N-benzylephedrine-promoted addition of dimethylzinc to a diphenylphosphinoylimine derived from 3-methoxybenzaldehyde is described. The enantiomeric ratio of the key amine fragment was determined to be 93:7 (86% ee), favoring the (R)-enantiomer by derivatization and chiral stationary phase HPLC analysis.

A stereo-controlled synthesis of 2,4-dimethyl-4-hydroxy-16- phenylhexadecanoic acid 1,4-lactone and its PPAR activities

A novel class of natural PPAR agonists, 2,4-dimethyl-4-hydroxy-16- phenylhexadecanoic acid 1,4-lactone (1), were discovered in marine natural product libraries. The synthesis of 1 was accomplished starting from vinylmethyl ketone. Ring formation of the α,γ dialkyl γ-lactone was achieved via the stereo-controlled reaction of a ketyl radical anion with a chiral methacrylate. In the PPAR agonistic assay, the most potent of the four stereoisomers had EC50 values of 12 μM for mPPARα, 9 μM for mPPARδ and >100 μM for mPPARγ.

Enantiospecific Stereodivergent Synthesis of trans- and cis-N(2), 3-Dimethyl- 4-phenyl-1, 2, 3, 4-tetrahydroisoquinolines

The acid-promoted cyclizations of a range of N-benzylethanolamines (derived from pseudoephedrine or ephedrine) give the corresponding trans-N(2), 3-dimethyl-4-phenyl-1, 2, 3, 4- tetrahydroisoquinolines with high levels of diastereoselectivity and in good yields of isolated product. The cyclizations of the corresponding chromium tricarbonyl complexes are rendered completely stereoselective. Acidpromoted cyclization of N-(3′, 4′- dimethoxybenzyl) ephedrine and its chromium tricarbonyl complex occur with complementary diastereoselectivities to give trans- and cis-N(2), 3-dimethyl-4- phenyl-6, 7-dimethoxy-1, 2, 3, 4-tetrahydro- isoquinoline, respectively, in >99:1 d.r. The latter is consistent with a "double inversion" mechanism, which involves neighboring group participation by the chromium tricarbonyl moiety followed by rearomatization to give the corresponding cis-tetrahydroisoquinoline with overall retention of configuration.

N-Pyridylmethylephedrine derivatives in the catalytic asymmetric addition of diethylzinc to aldehydes and diphenylphosphinoylimines

N-Pyridylmethyl-substituted Ephedra derivatives were synthesized by either direct alkylation or reductive alkylation of (1R,2S)-norephedrine, (1S,2S)-pseudo norephedrine, and (1R,2S)-ephedrine. These derivatives were then employed in asymmetric addition reactions with diethylzinc and aldehydes and diphenylphosphinoylimines. The use of the diastereomers from the Ephedra family allowed for a systematic evaluation of the contribution of the N-pyridylmethyl.

Development of a solid-phase 'asymmetric resin-capture-release' process: Application of an ephedrine chiral resin in an approach to γ- butyrolactonest

The potential of a solid-phase asymmetric resin-capture-release strategy for high-throughput synthesis has been evaluated. Fukuzawa's Sm(II)-mediated, asymmetric approach to γ-butyrolactones was selected to illustrate the feasibility of such a process. α,β-Unsaturated esters immobilised on an ephedrine chiral resin have been applied in an asymmetric approach to γ-butyrolactones. Lactone products are obtained in moderate isolated yields with selectivities up to 96% ee. In addition, we have shown that the ephedrine resin can be conveniently recovered and recycled although in some cases lower yields were obtained on reuse of the chiral resin. A short synthesis of a moderate DNA-binding microbial metabolite using asymmetric resin-capture-release is also described.

Diastereoselectivity in the reduction of α-oxy- and α-amino-substituted acyclic ketones by polymethylhydrosiloxane

Diastereoselectivity in the reduction of α-alkoxy-, α-acyloxy-, and α-alkylamino-substituted ketones with polymethylhydrosiloxane (PMHS) in the presence of fluoride ion catalysis was investigated. High syn-selectivity was observed in the reduction of α-alkoxy, α-acyloxy, and α-dialkylamino ketones. Reduction of α-monoalkylamino ketone proceeded in anti-selective manner with moderate selectivity. The observed selectivity is explained based on Felkin-Anh and Cram-chelate models.

Stereoselective formation and rearrangement of morpholinium ylides derived from copper carbenoids

Amino diazoacetoacetates 4a-e and 7a,b were prepared from readily available amino alcohols and subjected to copper-catalyzed carbene-transfer reaction. Substrates 4c-e furnished the morpholin-2-ones 5c-e in good yield via the corresponding cyclic ammonium ylides, albeit with poor diastereoselectivity. Substrates 4a,b failed to provide the corresponding morpholinones, perhaps as a result of steric congestion. Cyclic substrates 7a,b underwent conversion to bicyclic morpholinones 8 and 9 in good yield and with moderate to good diastereoselectivity. This result is rationalized via control of the transiently stereogenic ammonium center of the intermediate bicyclic ylides.

Synthesis of N-(dialkylaminoalkyl)alcohols by homogeneously catalyzed hydrogenolysis of cyclic N,O-acetals

The homogeneously catalyzed hydrogenation of 1,3-oxazolidines affording unsymmetrically substituted 2-N-(dialkylamino)ethanols is reported showing for the first time that Rh(I) catalysts based on chelating diphosphines can be advantageous for this reaction.

The Reductive Cleavage of Cyclic Aminol Ethers to N,N-Dialkylamino-derivatives: Modifications to the Eschweiler-Clarke Procedure

The reductive cleavage of cyclic aminol ethers to give N-alkylamino-derivatives in very high yields can be achieved using chlorotrimethylsilane in the presence of sodium cyanoborohydride: in the case of cyclic aminol ethers derived from formaldehyde the Eschweiler-Clarke reaction can be carried out in formic acid heated under reflux in the absence of formaldehyde.

Reactions of aldehydes with diethylzinc catalysed by polymer-supported ephedrine and camphor derivatives: Comparisons of enantiomeric excesses achieved with various supports: Optimisation of support parameters to enable high enantiomeric excesses to be obtained

The reactions of benzaldehyde with diethylzinc catalysed by PS ephedrine or camphor derivatives have been investigated in some depth in order to identify the crucial factors necessary to successfully prepare PS chiral catalysts for such reactions. The most important factor is found to be a favourable interaction of the polymer matrix with the reaction solvent so that the polymer will dissolve or swell to allow the other reactants easy access to the catalytic sites. Accordingly toluene is a better reaction solvent than hexane. The ephedrine-derived catalytic groups reduce the solubility of the linear polymers in toluene and, almost certainly, the swelling properties of the crosslinked polymers. Thus, of the polymers investigated the better linear ones had ca. 1.5 mmol per g of catalyst sites and the better insoluble ones were 1% crosslinked gels with ca. 1.0 mmol per g of catalyst sites. Site-site interactions and microenvironmental effects do not appear to play a major role in these PS reaction systems. For the reaction of benzaldehyde with diethylzinc, using the best linear PS ephedrine derivatives 10f, 10g or 11e affords 1-phenylpropanol (1) with 83-88% enantiomeric excesses (ee)s of the (R)-enantiomer; using the best linear PS camphor derivative 21 affords the alcohol 1 with a 98% ee of the (S)-enantiomer; using the best crosslinked PS ephedrine derivative 12a affords the alcohol 1 with a 78-81% ee and using the best crosslinked PS camphor derivative 22 affords alcohol 1 with a 97% ee of the (S)-enantiomer. These values are close to those obtained using analogues of non-polymeric catalysts under similar reaction conditions.