1384457-51-5

Upstream product

• 1313374-17-2 N,N-dimethyl-2-methyl-3-(3-methoxyphenyl)valeramide 
• 96251-92-2 (E)-3-(3-hydroxyphenyl)acrylic acid ethyl ester 
• 208836-69-5 3-(3'-benzyloxyphenyl)-(E)-propenoic acid ethyl ester 
• 1384457-44-6 (2R,3R)-3-(3-benzyloxyphenyl)-2-methylpent-4-enoic acid 
• 1384457-45-7 (2R,3R)-3-(3-benzyloxyphenyl)-2-methylpent-4-enoic acid (R)-1-phenylethylamine salt 
• 155697-42-0 (E)-3-(3-(benzyloxy)phenyl)prop-2-en-1-ol 
• 1384457-52-6 (1R,2R)-3-(3-hydroxyphenyl)-2-methyl-pentanoic acid 
• 1384457-48-0 (2E)-3-(3-benzyloxyphenyl)prop-2-en-1-yl propionate 
• 124-40-3 dimethyl amine 
• 1383959-11-2 (4R)-3-[(2E)-3-[3-(benzyloxy)phenyl]acryloyl]-4-phenyl-oxazolidin-2-one 
• 1383959-12-3 (4R)-3-[(3R)-1-oxo-3-[3-(phenylmethoxy)phenyl]pentyl]-4-phenyl-2-oxazolidinone 
• 1383959-14-5 (4R)-3-[(2R,3R)-2-methyl-1-oxo-3-[3-(phenylmethoxy)phenyl]pentyl]-4-phenyl-2-oxazolidinone 
• 1367878-82-7 C₁₉H₂₁ClO₂ 
• 1367878-84-9 (αR,βR)-β-ethyl-α-methyl-3-(phenylmethoxy) benzenepropanoic acid 

Downstream Products

• 175591-09-0 tapentadol hydrochloride 

Relevant academic research and scientific papers

Substituted n-pentanamide compounds, preparation method and the use thereof

The present invention relates to a (2R, 3R)-3-(3-substituted phenyl)-2-methyl n-pentanamide compounds as shown in the formula I and the preparation method thereof, wherein, the substituents are as defined in the specification, the present invention further relates to a use of the above compounds for the preparation of tapentadol II or its pharmaceutically acceptable salt, and the intermediates involved in the preparation process.

SUBSTITUTED N-PENTANAMIDE COMPOUNDS, PREPARATION METHODS AND USES THEREOF

The present invention relates to a (2R, 3R)-3-(3-substituted phenyl)-2-methyl n-pentanamide compounds as shown in the formula I and the preparation method thereof, wherein, the substituents are as defined in the specification, the present invention further relates to a use of the above compounds for the preparation of tapentadol II or its pharmaceutically acceptable salt, and the intermediates involved in the preparation process.

A NOVEL PROCESS FOR THE PREPARATION OF TAPENTADOL OR A PHARMACEUTICALLY ACCEPTABLE SALT THEREOF

Disclosed herein is a novel, commercially viable and industrially advantageous process for the preparation of 3-[(1R,2R))-3-(dimethylamino)-1-ethyl-2-methylpropyl]phenol (Tapentadol), or a pharmaceutically acceptable salt thereof, in high yield and purity. Also described are novel intermediates useful for preparing tapentadol or a pharmaceutically acceptable salt thereof.

O-SUBSTITUTED (2R,3R)-3-(3-HYDROXYPHENYL)-2-METHYL-4-PENTENOIC ACIDS AND A METHOD OF OBTAINING THE SAME

The compounds of general formula II are new and represent important intermediates in the synthesis of tapentadol. In the synthesis of tapentadol of formula I and its pharmaceutically acceptable salts, O-protected (2R,3R)-acids of general formula II, in step A, are reacted in an inert organic solvent with an activating agent, optionally in presence of a catalyst or a base; in step B, the obtained compounds of general formula V, wherein R has the above mentioned meaning and X stands for chlorine or alkoxycarbonyloxyl group O-CO-OR1 or pivaloyloxyl O-CO-t-Bu group, wherein R1 is methyl or ethyl, are reacted with dimethylamine or its salts optionally in presence of a base; in step C, the obtained N, N-dimethylamides of general formula VI, wherein R has the above mentioned meaning, are reduced by means of hydride agents in a suitable solvent; in step D, the produced alkeneamines of general formula VII, wherein R has the above mentioned meaning, are hydrogenated on a metal catalysts in a suitable solvent; and, finally, in step E, the produced alkaneamines of general formula VIII, wherein R has the above mentioned meaning, are O-dealkylated by means of dealkylating agents, and, if required, the obtained tapentadol is converted by the action of a pharmaceutically acceptable acid to respective salts, e.g. hydrochloride.

Process for Preparing Substituted 3-(1-amino-2-methylpentane-3-yl)phenyl Compounds

A process for the preparation of substituted 3-(1-amino-2-methylpentane-3-yl)phenyl compounds.