2-methoxy-3-phenylpropyl

Bis[2-methoxy-3-phenylpropyl] Ditellurium4 2.0 g tellurium dioxide (12.5 mmol) are dissolved in 10 ml concentrated hydrochloric acid. The yellow solution is diluted with 40 ml methanol. 1.75 mg (14.8 mmol) allylbenzene are addded, the mixture is refluxed for 24 h, and then cooled to 20°. The yellowish homogeneous solution is poured into a separatory funnel containing 5 g disodium disulfitc in 100 ml water and 100 m/ dichloromethane. The mixture is shaken, the red dichloromethane phase separated, dried, and evaporated. The red, oily residue is flash chromatographed on silica gel with dichloromethane as the mobile phase yield 80%. 

Methoxy-3-phenylpropyl Tellurium Trichloride1 2.0 g (12.5 mmol) tellurium dioxide are dissolved in 10 m/ concentrated hydrochloric acid and 40 ml methanol are added. 1.75 g (14.8 mmol) of allylbenzene are added. The mixture is refluxed for 24 h and then cooled to 20°. This solution containing the 2-methoxy-3-phenylpropyl tellurium trichloride was reduced with aqueous disodium disulfite to the ditellurium compound. 

Methoxy-3-phenylpropyl Tellurium Trichloride4 A stirred solution of 0.50 g (1.81 mmol) bis [2-methoxy-3-phenylpropyl] ditellurium in a mixture of 2 m/ carbon tetrachloride and 6 ml hexane is cooled to 0°. 0.37 g (2.74 mmol) sulfuryl chloride dissolved in 2 ml hexane are added. After cooling in a freezer, the product was isolated yield 91% m.p. 119°... 

Glowa J., Fantegrossi W., Lewis D., Matecka D., Rice K., Rothman R. Sustained decrease in cocaine-maintained responding in rhesus monkeys with l-[2]-bis(4-flourophenyl)methoxy[ethyl]-4-(3-hydroxy-3-phenylpropyl)piperazinyldecanoate, a long-acting ester derivative of GBR 12909. J. Med. Chem. 39 4689, 1996. 

Hsin, L.-W., Dersch, C.M., Baumann, M.H. et al. (2002) Development of long-acting dopamine transporter ligands as potential cocaine-abuse therapeutic agents chiral hydroxyl-containing derivatives of l-[2-[bis (4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine and l-[2-(diphenylmethoxy)ethyl]-4-(3-phe-nylpropyl)piperazine. Journal of Medicinal Chemistry, 45 (6), 1321-1329. 

The presence of a 4-methoxy substituent on the 2-phenylethyloxyl or 3-phenylpropyl-oxyl side chains radically altered the course of these cyclizations (Scheme 4). 31a and 31b afforded the spiro-fused ring systems 32 and 33 in 26 and 69% yields, respectively, as the only cyclization products. With this substituent, cyclization onto the activated ipso positions was favoured over direct attack, even where the strained transition state for Atj -5 cyclization of 31a to 32 was involved. Demethylation of the intermediate spirocyclohexa-dienyl cation is favoured over rearrangement in these cases. Kikugawa and coworkers effected the formation of 32 (82%) and 33 (39%) with reverse efficiencies using AgaCOs in TFA . 

RBSctions of Radical Anions With Radicals. The coupling of arene or alkene radical anions with radicals is an important reaction, and one that has significant synthetic potential. For example, radicals formed by nucleophilic capture of radical cations couple with the acceptor radical anion, resulting in (net) aromatic substitution. Thus, the l-methoxy-3-phenylpropyl radical (113 R = H) couples with dicyanobenzene radical anion loss of cyanide ion then generates the substitution product 132.2 + ... 

Rangisetty JB, Dukat M, Dowd CS, et al. l-[2-Methoxy-5-(3-phenylpropyl)]-2-aminopropane unexpectedly shows 5-HT2A serotonin receptor affinity and antagonist character. J Med Chem 2001 44 3283-3291. 

The preparation of the Step 1 co-reagent, l-(4-aminomethylphenyl)-3-(3-hydroxy-3-phenylpropyl)-4-(4-methoxy-phenyl)azetidin-2-one and other hydroxy-substituted azetidinone derivatives useful in treating hypocholesterolemic diseases is described by Rosenblum (1). 

The reaction between dimethyl 2-bromo-l-phenylpropylidenemalonate and sodium methoxide in methanol affords a complex reaction mixture consisting of dimethyl 2-methyl-3-phenyl-2-cyclopropene-l,l-dicarboxylate (303,19%), dimethyl (2,2-dimethoxy-l-methyl-2-phenylethyl)malonate (304, 4%), dimethyl 2-methoxy-l-phenylpropyl-idenemalonate (305, 11%), dimethyl 2-bromo-l-phenyl-1-propenylmalonate (306 -isomer, 10% Z-isomer, 13%) and dimethyl (l,2-dimethoxy-l-phenylpropyl)malonate... 

Staggered configurations have also been observed for the tricarbonyl chromium complexes of phenanthrene 294, 295), 9,10-dihydro-phenanthrene 293, 295), anthracene 202), naphthalene 262), and 1-aminonaphthalene 58). The eclipsed configuration has been observed for the tricarbonyl complexes of anisole (57, 229), toluidine 60, 61), methylbenzoate (59), o-methoxyacetylbenzene, o-hydroxyacetylbenzene 101), 2-methoxy-[l-hydroxy-ethyl]benzene (99), and 2-methyl-[l-hydroxy-l-phenylpropyl]benzene (97). It is apparent that the orientation of the chromium tricarbonyl moiety is in many cases controlled by the substituents on the ring to which it is coordinated, and this has been attributed to mesomeric electron repulsion or withdrawal by the substituents 374). 

SD Menacherry, JB Justice Jr. In vivo microdialysis and thermospray tandem mass spectrometry of the dopamine uptake blocker l-[2-[bis(4-fluorophenyl) methoxy]-ethyl]-4-(3-phenylpropyl)-piperazine (GBR-12909). Anal Chem 62 597-601,1990. 

RS, 2RS, 3RS)-3-Hydroxy-2-methyl-1-phenylpentyl benzoate 3s and (1SR, 2RS, 3RS)-1-Ethyl-3-hydroxy-2-methyl-3-phenylpropyl benzoate 3a. To a solution of Ti(OiPr)4 (0.32 mL, 1 mmol) in 1-tert-butoxy-2-methoxy ethane (1.5 mL) was carefully added BuLi (0.64 mL, 1 mmol) in hexane under Ar. After stirring for 30 min at 20°C, ketoalcohol 1 (0.5 mL, 5 mmol) and then Ph-CHO 2 (1 mL, 10 mmol) were added. The solution was stirred for 24 h at 20°C and after usual work up the product was chromatographed (silica gel, hexane iPrOH 95 5) to afford 3 and 3a in ratio 5 95. 

The pitfalls that can accompany the development of the amorphous form of a drug substance were shown for the capsule formulation of (3i ,4.Sy)-l,4-bis(4-methoxy-phenyl)-3-(3-phenylpropyl)-2-azetidi-none [17]. A variety of spectroscopic techniques were used to study the amorphous-to-crystalline phase transition, and it was determined that problems encountered with dissolution rates could be related to the amount of crystalline material generated in the formulation. 

Synonyms. 4-(2-Methoxy-2-phenylethyl)-a-(methoxyphenyl-methyl)-l-piperazeneethanol l-(2-Methoxy-2-phenylethyl)-4-(2-hydroxy-3-methoxy-3-phenylpropyl) piperazine. 

FigureS, Absorption spectrum of the S-methoxy-l-phenylpropyl radical generated by reaction of the 3-methylstyrene radical cation with methanol in TFE.

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