175590-76-8

Usage

Uses

Used in Pharmaceutical Industry:
(alphaR)-rel-alpha-[(1R)-2-(Dimethylamino)-1-methylethyl]-alpha-ethyl-3-methoxybenzenemethanol is used as a potential active pharmaceutical ingredient for its complex structure and chiral nature, which may contribute to specific biological activities and therapeutic effects.
Used in Research Applications:
(alphaR)-rel-alpha-[(1R)-2-(Dimethylamino)-1-methylethyl]-alpha-ethyl-3-methoxybenzenemethanol serves as a valuable research tool in the field of organic chemistry, particularly in studies related to stereochemistry, chiral synthesis, and the investigation of the effects of stereoisomers on chemical reactivity and biological activity.
Used in Chemical Synthesis:
(alphaR)-rel-alpha-[(1R)-2-(Dimethylamino)-1-methylethyl]-alpha-ethyl-3-methoxybenzenemethanol can be utilized as a key intermediate in the synthesis of other complex organic molecules, taking advantage of its unique functional groups and chiral properties.

InChI:InChI=1S/C15H25NO2/c1-6-15(17,12(2)11-16(3)4)13-8-7-9-14(10-13)18-5/h7-10,12,17H,6,11H2,1-5H3/t12-,15-/m1/s1

Upstream product

• 850222-40-1 (2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone 
• 925-90-6 ethylmagnesium bromide 
• 197145-37-2 3-(dimethylamino)-1-(3-methoxyphenyl)-2-methylpropan-1-one 
• 3027-13-2 1-(3-methoxyphenyl)propan-2-one 
• 850222-41-2 (S)-3-(dimethylamino)-1-(3-methoxyphenyl)-2-methylpropan-1-one (2R,3R)-O,O'-dibenzoyltartrate 
• 51690-03-0 1-(dimethylamino)-2-methylpentan-3-one 
• 36282-40-3 (3-methoxyphenyl)magnesium bromide 
• 2386-64-3 ethylmagnesium chloride 
• 175590-75-7 (2R,3R)/(2S,3S)-1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol hydrochloride 
• 175590-76-8 (2R,3R)/(2S,3S)-1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol 
• 1332841-01-6 (2S,3S)-1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol S-naproxen 
• 159144-11-3 (2S)-1-(dimethylamino)-2-methylpentan-3-one 
• 634921-25-8 (2R,3R)-1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol S-naproxen 
• 175590-75-7 (2R,3S)/(2S,3R)-1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol hydrochloride 

Downstream Products

• 809282-31-3 (E)-(2R)-[3-(3-methoxy-phenyl)-2-methyl-pent-3-enyl]-dimethyl-amine 
• 809282-30-2 (Z)-(2R)-[3-(3-methoxy-phenyl)-2-methyl-pent-3-enyl]-dimethyl-amine 
• 1332841-09-4 (+)-(2S,3S)-[3-(3-methoxyphenyl)-2-methylpentyl]-dimethylamine (-)-di-p-toluoyl-L-tartaric acid salt 

Relevant academic research and scientific papers

PROCESS FOR THE PREPARATION OF TAPENTADOL

Disclosed herein is an improved process for the preparation of 3-[(2R,3R)-1-(dimethylamino)-2-methylpentan-3-yl]phenol of Formula-I and its pharmaceutically acceptable salt which comprises the reaction of (S)-1-(dimethylamino)-2-methylpentan-3-one of formula VIII with 3-bromo anisole of formula II under Grignard conditions to get the compound (2S, 3R)-1-(dimethylamino)-3-(3-methoxyphenyl)-2-methyl pentan-3-ol of formula V followed by activation of the —OH group of the formula V to convert into sulfonate esters of formula IX, which are on reductive deoxygenation to yield (2R,3R)-3-(3-methoxyphenyl)-N,N,2-trimethylpentan-1-amine of formula VII and demethylation of formula VII to obtain the compound 3-[(2R,3R)-1-(dimethylamino)-2-methylpentan-3-yl]phenol of Formula-1.

A NOVEL STEREOSPECIFIC SYNTHESIS OF (-) (2S,3S)-1-DIMETHYLAMINO-3-(3-METHOXYPHENYL)-2-METHYL PENTAN-3-OL

The present invention relates to a novel stereospecific synthesis of (-) (2S,3S)-1-dimethylamino-3-(3-methoxyphenyl)-2-methyl pentan-3-ol an intermediate in the synthesis of 3-[(1R,2R)-3-(dimethylamino)-1-ethyl-2-methylpropyl]phenol.

PROCESS FOR THE PREPARATION OF TAPENTADOL

Disclosed herein is an improved process for the preparation of 3-[(2R,3R)-1- (dimethylamino)-2-methylpentan-3-yl] phenol of Formula - I and its pharmaceutically acceptable salt which comprises the reaction of (S)-1-(dimethylamino)-2-methylpentan- 3-one of formula VIII with 3 - bromo anisole of formula II under Grignard conditions to get the compound (2S, 3R)-1- (dimethylamino)-3-(3-methoxyphenyl)-2-methyl pentan-3- ol of formula V followed by activation of the -OH group of the formula V to convert into sulfonate esters of formula IX, which are on reductive deoxygenation to yield (2R,3R)-3- (3-methoxyphenyl)-N,N,2-trimethylpentan-1 -amine of formula VII and demethylation of formula VII to obtain the compound 3-[(2R,3R)-1-(dimethylamino)-2-methylpentan-3- yl]phenol of Formula - 1.

PRODRUGS OF OPIOIDS AND USES THEREOF

The present invention concerns prodrugs of opioid analgesics and pharmaceutical compositions containing such prodrugs. Methods for providing more consistent pain relief by increasing the bioavailability of the opioid analgesic with the aforementioned prodrugs are provided. The invention also provides for decreasing the adverse GI side effects of opioid analgesics.

IMPROVED RESOLUTION METHODS FOR ISOLATING DESIRED ENANTIOMERS OF TAPENTADOL INTERMEDIATES AND USE THEREOF FOR THE PREPARATION OF TAPENTADOL

Provided herein is an improved and industrially advantageous optical resolution method for resolving (2R,3R)/(2S,3S)-l-dimethylamino-3-(3-methoxyphenyl)-2- methylpentan-3-ol, and use thereof for the preparation of tapentadol or a pharmaceutically acceptable salt thereof. Provided further herein is an improved and industrially advantageous optical resolution method for resolving (2R,3R)/(2S,3S)-[3-(3-methoxyphenyl)-2- methylpentyl]-dimethylamine, and use thereof for the preparation of tapentadol or a pharmaceutically acceptable salt thereof. Disclosed also herein is an improved, commercially viable and industrially advantageous process for the preparation of tapentadol or a pharmaceutically acceptable salt thereof in high yield and purity.

AMINO ACID AND PEPTIDE CARBAMATE PRODRUGS OF TAPENTADOL AND USES THEREOF

Prodrugs of tapentadol with amino acids or short peptides, pharmaceutical compositions containing such prodrugs and a method for providing pain relief with the tapentadol prodrugs are provided herein. Prodrugs having side chains of valine, leucine, isoleucine and glycine amino acids and mono-, di- and tripeptides thereof are preferred. Additionally, methods for avoiding or minimizing the adverse gastrointestinal side effects associated with tapentadol administration, as well as increasing the oral bioavailability of tapentadol are provided herein.

Separation of Stereoisomeric N,N-Dialkylamino-2Alkyl-3-Hydroxy-3-Phenylalkanes

The invention concerns a method for the isolation of a stereoisomer from a mixture comprising the two stereoisomers of the general formulae (I-A) and (I-A′) and/or the two stereoisomers of the general formulae (I-B) and (I-B′) in which R1, R2 and R3, identical or different, are selected from the group consisting of —H, —F, —Cl, —C1-C6-alkyl, —S—C1-C6-alkyl, —OH, —O—C1-C6-alkyl, —O—C1-C6-alkylenephenyl, —OCO—C1-C6-alkyl, —OCON(C1-C6-alkyl)2 and —O—SiR8R9R10 (in which R8, R9 and R10, identical or different, are —C1-C6-alkyl or -phenyl);R4 is —H or —C1-C6-alkyl;R5 is —C1-C6-alkyl; andR6 and R7, identical or different, are —H or —C1-C6-alkyl; or their salts with organic or inorganic acids; comprising the step (a) manipulating the mixture ratio of the stereoisomers in the mixture so that at least one of the stereoisomers is present in an enantiomeric excess.

PREPARATION OF (2R,3R)-3-(3-METHOXYPHENYL)-N,N,2-TRIMETHYLPENTANAMINE

The present invention relates to an improved process for the preparation of (2R,3R)-3- (3-methoxyphenyl)-N,N,2-trimethylpentanamine which is an intermediate for the preparation of the analgesic tapentadol.

PROCESS FOR THE PREPARATION OF (1R,2R)-3-(3-DIMETHYLAMINO-1-ETHYL-2-METHYL-PROPYL)-PHENOL

The present invention relates to a process for the preparation of (1 R,2R)-3- dimethylamino-1-ethyl-2-methyl-propyl)-phenol.

SEPARATION OF STEREOISOMERIC N,N-DIALKYLAMINO-2-ALKYL-3-PHENYL ALKANES

The invention relates to a method for isolating a stereoisomer from a mixture comprising two stereoisomers of general formulas (I-A) and (I-A') and/or two stereoisomers of general formulas (I-B) and (I-B'), wherein R1, R2, and R3 are identical or different and are selected among the group comprising -H, -F, -Cl, -C1-C6 alkyl, -S-C1-C6 alkyl, -OH, -O-C1-C6 alkyl, -O-C1-C6 alkylene-phenyl, -OCO-C1-C6 alkyl, -OCON(C1-C6 alkyl)2, and -O-SiR8R9R10 (wherein R8, R9, and R10 are identical or different, representing -C1-C6 alkyl or -phenyl); R4 represents -H or -C1-C6 alkyl; R5 represents -C1-C6 alkyl; and R6 and R7 are identical or different, representing -H or -C1-C6 alkyl; or the salts thereof with organic or inorganic acids. The inventive method encompasses step (a) in which the mixing ratio of the stereoisomers in the mixture is influenced such that at least one of said stereoisomers is provided with excess enantiomers.