116539-56-1

Basic information

• Product Name: 3-METHYLAMINO-1-(2-THIENYL)-1-PROPANOL
• Synonyms: 1-β-Hydroxy-1-(2-thienyl)-3-MethylaMinopropane;2-ThiopheneMethanol, a-[2-(MethylaMino)ethyl]-;3-(methylamino)-1-(thiophen-2-yl)propan-1-ol
• CAS NO: 116539-56-1
• Molecular Formula: C₈H₁₃NOS
• Molecular Weight: 171.26
• Product Categories: Amines, Aromatics, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds
• Mol File: 116539-56-1.mol

Chemical Properties

• Boiling Point: 294.3°Cat760mmHg
• Flash Point: 131.8°C
• Appearance: /
• Density: 1.128g/cm³
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Methanol
• CAS DataBase Reference: 3-METHYLAMINO-1-(2-THIENYL)-1-PROPANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYLAMINO-1-(2-THIENYL)-1-PROPANOL(116539-56-1)
• EPA Substance Registry System: 3-METHYLAMINO-1-(2-THIENYL)-1-PROPANOL(116539-56-1)

Safety Data

• Hazardous Substances Data: 116539-56-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-METHYLAMINO-1-(2-THIENYL)-1-PROPANOL is used as a key intermediate in the synthesis of Duloxetine (D721000) derivatives. It plays a significant role in the production of these pharmaceutical compounds, which are known for their therapeutic applications in treating various medical conditions, such as depression, anxiety, and neuropathic pain. The unique structure of 3-METHYLAMINO-1-(2-THIENYL)-1-PROPANOL allows for the creation of diverse Duloxetine analogs with potential improvements in efficacy, safety, and pharmacokinetic properties.

Upstream product

• 645411-16-1 N-methyl-3-(thien-2-yl)-3-morpholino-propylamine hydrochloride 
• 74-89-5 methylamine 
• 260354-12-9 3-chloro-1-(thiophen-2-yl)propan-1-ol 
• 40570-64-7 3-chloro-1-(2-thienyl)propan-1-one 
• 89639-64-5 (E)-3-(thien-2-yl)prop-2-en-1-ol 
• 1124-65-8 3-(2-thienyl)-2-propenoic acid 
• 39511-07-4 (E)-2-(2-thienyl)ethylene-1-carbaldehyde 
• 1620141-95-8 C₂₀H₁₇NS 
• 1146983-61-0 3-methoxymethylamino-1-(2-thienyl)propan-1-ol 
• 663603-70-1 (Z)-3-(methylamino)-1-(thiophen-2-yl)prop-2-en-1-one 
• 625853-19-2 phenyl (RS)-N-methyl-N-[3-phenyloxycarbonyloxy-3-(thien-2-yl)propyl]carbamate 
• 88-15-3 2-Acetylthiophene 
• 98-03-3 thiophene-2-carbaldehyde 

Downstream Products

• 680624-71-9 (S)-MMAA (2R,3R)-(-)-O,O'-di-p-toluoyltartaric acid 
• 116817-13-1 duloxetine 
• 680624-70-8 (S)-MMAA (R)-α-methoxyphenylacetic acid 
• 116539-55-0 (S)-3-methylamino-1-(2-thienyl)-1-propanol 
• 116539-57-2 (R)-3-(methylamino)-1-(thiophen-2-yl)propan-1-ol 

Relevant articles and documents

Chemoenzymatic synthesis of (S)-duloxetine using carbonyl reductase from Rhodosporidium toruloides

A chemoenzymatic strategy was developed for (S)-duloxetine production employing carbonyl reductases from newly isolated Rhodosporidium toruloides into the enantiodetermining step. Amongst the ten most permissive enzymes identified, cloned, and overexpressed in Escherichia coli, RtSCR9 exhibited excellent activity and enantioselectivity. Using co-expressed E. coli harboring both RtSCR9 and glucose dehydrogenase, (S)-3-(dimethylamino)-1-(2-thienyl)-1-propanol 3a was fabricated with so far the highest substrate loading (1000 mM) in a space-time yield per gram of biomass (DCW) of 22.9 mmol L-1 h-1 g DCW-1 at a 200-g scale. The subsequent synthetic steps from RtSCR9-catalyzed (S)-3a were further performed, affording (S)-duloxetine with 60.2% overall yield from 2-acethylthiophene in >98.5% ee.

OLIGOMER-ARYLOXY-SUBSTITUTED PROPANAMINE CONJUGATES

The invention relates to (among other things) oligomer- aryloxy-substituted propanamine conjugates and related compounds. A conjugate of the invention, when administered by any of a number of administration routes, exhibits advantages over un-conjugated aryloxy-substituted propanamine compounds.

Total synthesis of fluoxetine and duloxetine through an in situ imine formation/borylation/transimination and reduction approach

We report efficient, catalytic, asymmetric total syntheses of both (R)-fluoxetine and (S)-duloxetine from α,β-unsaturated aldehydes conducting five sequential one-pot steps (imine formation/copper mediated β-borylation/transimination/reduction/oxidation) followed by the specific ether group formation which deliver the desired products (R)-fluoxetine in 45% yield (96% ee) and (S)-duloxetine in 47% yield (94% ee). This journal is the Partner Organisations 2014.

METHYLHYDROXYLAMINOPROPANOL DERIVATIVE AND ITS USE AS INTERMEDIATE FOR PREPARATION OF 3-METHYLAMINO-1-(2-THIENYL)PROPAN-1-OL

The present invention provides a methylhydroxylaminopropanol derivative and the methylhydroxylaminopropanol derivative of the present invention is used as an intermediate for preparation of 3-methylamino-1-(2-thienyl)propan-1-ol, which is an intermediate for preparation of (+)-(S)—N-methyl-3-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine oxalate. The present invention also provides a process for preparing 3-methylamino-1-(2-thienyl)propan-1-ol with higher yield and lower cost, wherein the methylhydroxylaminopropanol derivative is used as an intermediate.

5-Phenylthio-1,3-oxazinan-4-ones via hetero Diels-Alder reactions: synthesis of (R)- and (S)-Duloxetines and Fluoxetines

The synthesis of 5-phenylthio-1,3-oxazinan-4-ones, through a hetero Diels-Alder strategy, is described. The cycloadducts thus prepared have been shown to be useful intermediates for the synthesis of 1,3-aminoalcohols, valuable intermediates in the preparation of biologically significant molecules, e.g., optically active Duloxetines and Fluoxetines. In the course of this elaboration a novel microwave assisted desulfurization reaction is reported.

Practical synthesis of enantiopure γ-amino alcohols by rhodium-catalyzed asymmetric hydrogenation of β-secondary-amino ketones

(Chemical Equation Presented) Another way to antidepressants: A series of β-secondary-amino ketone hydrochlorides (e.g. 1) were hydrogenated with remarkably high enantioselectivities by using a Rh complex containing P-chiral bisphospholane 2. These results establish a short and practical means for the synthesis of enantiopure N-monosubstituted γ-amino alcohols (e.g. 3), which are key intermediates in the synthesis of important antidepressants. (nbd = norbornadiene; TON = turnover number).

Process for the preparation of enantiomerically pure 1-substituted-3-aminoalcohols

Provided is a process for the preparation of enantiomerically pure 1-substituted-3-amino-alcohols, particularly of (S)-(-)- and (R)-(+)-3-N-methylamino-1-(2-thienyl)-1-propanol, by asymmetrically hydrogenating salts of a carboxylic acids with an aminoketone of the formula wherein R1 is selected from the group consisting of 2-thienyl, 2-furanyl and phenyl, each optionally substituted with one or more halogen atoms and/or one or more C1-4-alkyl or C1-4-alkoxy groups, and wherein R2 is C1-4-alkyl or phenyl, each optionally substituted with one or more halogen atoms and/or one or more C1-4-alkyl or C1-4-alkoxy groups, and wherein the corresponding aminoalcohols are obtained by subsequent hydrolysis of their salts. Furthermore provided are salts of a carboxylic acid with said aminoketones and the aminoalcohols obtained by asymmetriacally hydrogenating said aminoketones, respectively.

PROCESS FOR PRODUCING N-MONOALKYL-3-HYDROXY-3-(2-THIENYL)PROPANAMINE AND INTERMEDIATE

The present invention provides a process for producing an N-monoalkyl-3-hydroxy-3-(2-thienyl)propanamine represented by General Formula (2): wherein R is C1-4 alkyl, comprising the step of reducing (Z)-N-monoalkyl-3-oxo-3-(2-thienyl)propenamine represented by General Formula (1): wherein R is as defined above. According to the present invention, an N-monoalkyl-3-hydroxy-3-(2-thienyl)propanamine which is for use as an intermediate for various pharmaceuticals can be produced in an industrially inexpensive and easy manner.

METHODS FOR THE PRODUCTION OF 3-METHYLAMINO-1-(THIENE-2-YL)-PROPANE-1-OL

The invention relates to enzymatic and non-enzymatic methods for the production of 3-methylamino-1-(thiene-2-yl)-propane-1-ol; in addition to enzymes for carrying out said method; nucleic acid sequences coding for said enzymes, expression cassettes containing them, vectors and recombinant hosts.

PROPANOLAMINE DERIVATIVES, PROCESS FOR PREPARATION OF 3-N-METHYLAMINO-1-(2-THIENYL)-1-PROPANOLS AND PROCESS FOR PREPARATION OF PROPANOLAMINE DERIVATIVES

The present invention provides means for preparing a racemate or an optically active substance (S- or R-isomer) of 3-N-methylamino-1-(2-thienyl)-1-propanol represented by the following general formula (I): wherein R1 represents any of a hydrogen atom, a C1-8 acyl group, a substituted or substituted C1-8 alkyloxycarbonyl group and a substituted or substituted phenyloxycarbonyl group and R2 represents any of a hydrogen atom, a C1-8 alkyl group, a substituted or substituted benzyl group, a C1-8 acyl group, a substituted or substituted C1-8 alkyloxycarbonyl group and a substituted or substituted phenyloxycarbonyl group, with the exception that R1 is a hydrogen atom and R2 is a methyl group or a hydrogen atom, in a simple manner at low cost and in high yield.