809282-20-0

Basic information

• Product Name: (2S,3R)-1-(Dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol
• Synonyms: (2S,3R)-1-(Dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol;(2R,3S)-1-(DiMethylaMino)-3-(3-Methoxyphenyl)-2-Methyl-3-pentanol hydrochloride;Benzenemethanol, α-[(1S)-2-(dimethylamino)-1-methylethyl]-α-ethyl-3-methoxy-, (αR)-;(2S)-1-(dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol;(2R,3S)-1-(Dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol;(2S ,3R)-1 -(Dimethylamino}-3-(3-methoxyphenyl)-2-methylpentan-3-01
• CAS NO: 809282-20-0
• Molecular Formula: C₁₅H₂₅NO₂
• Molecular Weight: 251
• Mol File: 809282-20-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 362.9±37.0 °C(Predicted)
• Appearance: /
• Density: 1.000
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.27±0.29(Predicted)
• CAS DataBase Reference: (2S,3R)-1-(Dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R)-1-(Dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol(809282-20-0)
• EPA Substance Registry System: (2S,3R)-1-(Dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol(809282-20-0)

Safety Data

• Hazardous Substances Data: 809282-20-0(Hazardous Substances Data)

Usage

General Description

The chemical compound "(2S,3R)-1-(Dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol" is a chiral alcohol with a molecular formula of C14H23NO2. It consists of a dimethylamino group, a methoxyphenyl group, and a methylpentanol group. (2S,3R)-1-(Dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol is commonly used in organic synthesis as a chiral building block, and it is also utilized in the pharmaceutical industry for the production of certain medications. Its stereochemistry and structure make it a valuable intermediate in the synthesis of various biologically active compounds.

Upstream product

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

Downstream Products

• 809282-45-9 (2S,3R)-1-(dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol hydrochloride 
• 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 
• 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 

Relevant articles and documents

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.

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.