51690-03-0

Usage

Synthesis Reference(s)

Tetrahedron Letters, 23, p. 547, 1982 DOI: 10.1016/S0040-4039(00)86885-9

InChI:InChI=1/C8H17NO/c1-5-8(10)7(2)6-9(3)4/h7H,5-6H2,1-4H3

Upstream product

• 50-00-0 formaldehyd 
• 506-59-2 N,N-dimethylammonium chloride 
• 96-22-0 pentan-3-one 
• 17510-47-3 3-trimethylsilyloxy-2-pentene 
• 25468-31-9 N-methyl-N-methylenemethanaminium 2,2,2-trifluoroacetate 
• 51-80-9 bis-(dimethylamino)methane 
• 78024-10-9 cis-(n-Bu)2BOC(Et)CHCH₃ 
• 56275-84-4 N-(butoxymethyl)dimethylamine 
• 51425-53-7 (E)-3-[(trimethylsilyl)oxy]pent-2-ene 
• 30354-18-8 N,N-dimethyl(methylene)ammonium chloride 
• 159144-11-3 (2S)-1-(dimethylamino)-2-methylpentan-3-one 
• 159144-11-3 (R)-1-(dimethylamino)-2-methylpentan-3-one 

Downstream Products

• 67960-91-2 2.3.5-Trimethyl-4-oxo-cyclohex-2-enessigsaeure 
• 76919-85-2 1-(2-Methyl-oxiranyl)-propan-1-one 
• 175590-75-7 1-dimethylamino-3-(3-methoxyphenyl)-2-methyl-3-pentanol hydrochloride 
• 197145-32-7 (2RS,3RS)-3-(3-difluoromethyl-phenyl)-1-dimethylamino-2-methyl-pentan-3-ol hydrochloride 
• 433936-26-6 (2RS,3RS)-1-dimethylamino-2-methyl-3-(3-methylsulphanylphenyl)-pentan-3-ol Hydrochloride 
• 175590-76-8 (2R,3S)-1-dimethylamino-3-(3-methoxy-phenyl)-2-methyl-pentan-3-ol 
• 809282-20-0 (2S,3R)-1-(dimethylamino)-3-(3-methoxyphenyl)-2-methyl pentan-3-ol 
• 454221-08-0 (-)-(2S,3S)-1-dimethylamino-3-(3-methoxyphenyl)-2-methyl-pentan-3-ol 
• 433936-14-2 (+)-(2R,3R)-1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol 
• 175590-75-7 (2R,3R)/(2S,3S)-1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol hydrochloride 
• 433936-25-5 (2RS,3RS)-3-(3,4-dichlorophenyl)-1-dimethylamino-2-methylpentan-3-ol Hydrochloride 

Relevant academic research and scientific papers

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.

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.

Unique reactivity of aminoketones in the trifluoromethylation with trialkyl(trifluoromethyl)silanes

Aminoketones were trifluoromethylated by using trialkyl(trifluoromethyl) silanes without any reaction promoters. Formation of cyclic intermediates is proposed to be possible transition states in this reaction. Moderate diastereoselectivities were observed in the trifluoromethylation of the aminoketones having a side chain.

Mannich Reaction of Carbonyl Compounds via Boron Enolates and N,N,N',N'-Tetramethyldiaminomethane

A variety of carbonyl compounds undergo N,N-dimethylaminomethylation in moderate to good yields by the Mannich reaction involving boron enolates and N,N,N',N'-tetramethyldiaminomethane in dichloromethane.

A Convenient Regioselective Synthesis of Mannich Bases

A new, convenient regioselective process for aminomethylation of ketones is reported, involving the in situ formation of silyl enol ethers and iminium salts.

Carbon-Carbon Bond Formation by the Use of Chloroiodomethane as a C1 Unit. III. A Convenient Synthesis of the Mannich Base from Enol Silyl Ether by a Combination of Chloroiodomethane and N,N,N',N'-Tetramethylmethanediamine

The Mannich dimethylaminomethylation of carbonyl compounds is conveniently carried out via enol trimethylsilyl ethers by a combination of chloroiodomethane (CH2ClI) and N,N,N',N'-tetramethylmethanediamine (TMMD) in DMSO as the solvent at ambient temperatute.The mechanism of the transformation is discussed on the basis of product analysis and 1H NMR spectral studies.The reagent system CH2ClI/TMMD also provides a convenient route to the Eschenmoser's salt ().

A NOVEL AMINOMETHYLATION OF SILYL ENOL ETHERS WITH AMINOMETHYL ETHERS CATALYZED BY IODOTRIMETHYLSILANE OR TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE

The iodotrimethylsilane-catalyzed reaction of silyl enol ethers with aminomethyl ethers in acetonitrile gives aminomethylation products of the corresponding ketones readily.The reaction can also be catalyzed by trimethylsilyl trifluoromethanesulfonate in dichloromethane.

THE MANNICH REACTION OF CARBONYL COMPOUNDS VIA SILYL ENOL ETHERS BY A COMBINATION OF CHLOROIODOMETHANE AND N,N,N',N'-TETRAMETHYLDIAMINOMETHANE

The Mannich dimethylaminomethylation of carbonyl compounds is conveniently carried out via trimethylsilyl enol ethers by a combination of chloroiodomethane and N,N,N',N'-tetramethyldiaminomethane in DMSO or DMF as the solvent at ambient temperature.