809282-20-0

Usage

Uses

Used in Organic Synthesis:
(2S,3R)-1-(Dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol is used as a chiral building block in organic synthesis for the creation of enantiomerically pure compounds. Its unique stereochemistry allows for the development of complex molecules with specific biological activities.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (2S,3R)-1-(Dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol is utilized for the production of certain medications. Its structural features contribute to the development of drugs with targeted therapeutic effects, potentially leading to improved treatments for various medical conditions.
Used in the Synthesis of Biologically Active Compounds:
(2S,3R)-1-(Dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol is used as an intermediate in the synthesis of biologically active compounds. Its unique structure and stereochemistry enable the creation of molecules with specific interactions and activities, which can be applied in various therapeutic areas.

Upstream product

• 850222-40-1 (2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone 
• 925-90-6 ethylmagnesium bromide 
• 2386-64-3 ethylmagnesium chloride 
• 51690-03-0 1-(dimethylamino)-2-methylpentan-3-one 
• 36282-40-3 (3-methoxyphenyl)magnesium bromide 
• 2398-37-0 3-methoxyphenyl bromide 
• 159144-11-3 (2S)-1-(dimethylamino)-2-methylpentan-3-one 

Downstream Products

• 809282-45-9 (2S,3R)-1-(dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol hydrochloride 
• 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 
• 1360589-13-4 (2S,3R)-1-(dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-yl 4-methylsulfonate 
• 175591-09-0 tapentadol hydrochloride 
• 175591-23-8 tapentadol 
• 175591-22-7 (βR,γR)-γ-ethyl-N,N,β-trimethyl-3-methoxybenzenepropanamine 

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.

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.

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.