146432-17-9

Usage

Uses

Used in Pharmaceutical Industry:
Morpholine, 4-[(2S)-2-hydroxy-1-oxopropyl]is used as a stabilizer in pharmaceutical products for its ability to maintain the stability and efficacy of medications, ensuring their safety and effectiveness for consumers.
Used in Oil and Gas Industry:
In the oil and gas industry, Morpholine, 4-[(2S)-2-hydroxy-1-oxopropyl]is utilized as a corrosion inhibitor to protect pipelines and equipment from the damaging effects of corrosive substances, thereby extending their service life and reducing maintenance costs.

Upstream product

• 110-91-8 morpholine 
• 687-47-8 (S)-Ethyl lactate 
• 27871-49-4 (S)-Methyl lactate 
• 97-64-3 ethyl 2-hydroxypropionate 

Downstream Products

• 295788-49-7 N-((2S)-2-p-toluenosulfonyloxypropanoyl)morpholine 
• 295788-52-2 2-((R)-1-morpholinocarbonylethoxy)-4-phthalimidomethylnitrobenzene 
• 295788-54-4 2-((R)-1-morpholinocarbonylethoxy)-4-tert-butoxycarbonylaminomethylnitrobenzene 
• 295788-51-1 2-((R)-1-morpholinocarbonylethoxy)-4-methanesulfonyloxymethylnitrobenzene 
• 295788-53-3 2-((R)-1-morpholinocarbonylethoxy)-4-aminomethylnitrobenzene 
• 295788-50-0 2-((R)-1-morpholinocarbonylethoxy)-4-hydroxymethylnitrobenzene 

Relevant academic research and scientific papers

Asymmetric synthesis of naproxen via a pinacol-type reaction

An asymmetric pinacol-type rearrangement was used in the synthesis of (S)-naproxen. The pinacol-type reaction of a sec-tert vicinal diol provided an α-aryl ketone wich was oxidized with sodium hypochlorite in the presence of methanol to the methyl ester of naproxen.

A PROCESS FOR THE MANUFACTURE OF POSACONAZOLE

The present invention discloses an improved process for the manufacture of Posaconazole, an anti-fungal agent belonging to the category of substituted Tetrahydrofuran Triazole compound. The present invention further describes preparation of formula A and formula B, the key intermediates in the preparation of Posaconazole. The invention also discloses novel intermediates that are useful in the synthesis of Posaconazole.

FORUMLATIONS

This invention relates to the use of lactamide compounds of formula (I): CH3CH(OH)C(=O)NR1R2, where R1 and R2 are each independently hydrogen; or C1-6 alkyl, C2-6 alkenyl or C3-6 cycloalkyl, each of which is optionally substituted by up to three substituents independently selected from phenyl, hydroxy, C1-5 alkoxy, morpholinyl and NR3R4 where R3 and R4 are each independently C1-3 alkyl; or phenyl optionally substituted by up to three substituents independently selected from C1-3 alkyl; or R1 and R2 together with the nitrogen atom to which they are attached form a morpholinyl, pyrrolidinyl, piperidinyl or azepanyl ring, each of which is optionally substituted by up to three substituents independently selected from C1-3 alkyl, in formulations to reduce the toxicity associated with other formulation components; to the use of certain lactamide compounds as solvents, especially in formulations, particularly in agrochemical formulations and in environmentally friendly formulations; to novel lactamide compounds; and to processes for preparing lactamide compounds.

Synthesis of β-amino alcohols via the reduction of lactamides derived from ethyl (2S)-lactate with borane-methyl sulfide

Reactions of ethyl (2S)-lactate with various amines affords lactamides that are reduced with borane-methyl sulfide in the presence of boron trifluoride etherate to generate enantiomerically pure β-amino alcohols in good yield. Georg Thieme Verlag Stuttgart.

STEREOSELECTIVE SYNTHESIS OF 1-[6-ETHYL-1,2-DIHYDROXY-PROPYL)-PYRIDIN-3-YL]-3-[2-(4-METHYL-PIPERAZIN-1-YL)-BENZYL]-PYRROLIDIN-2-ONE

The present invention is related to the stereospecific preparation of 1-[6-(1- ethyl-1,2-dihydroxy-propyl)-pyridin-3-yl]-3-[2-(4-methyl-piperazin-1-yl)-benzyl]- pyrrolidin-2-one, and the intermediates thereof. Another aspect of the invention relates to 1-[6-(1 -ethyl- 1,2-dihydroxy-propyl)-pyridin-3-yl]-3-[2-(4-methyl-piperazin-1- yl)-benzyl]-pyrrolidin-2-one, wherein the carbon atoms having the 1,2-dihydroxy substituents are any of the four diastereomers selected from (R,R), (R,S), (S,R), and (S, S), wherein the carbon three of the pyrrolidin-2-one is (R) or (S), pharmaceutically acceptable salts thereof, solvates thereof, pharmaceutical compositions containing them, and methods using them for in treating or preventing depression, anxiety, obsessive compulsive disorder (OCD) and other disorders for which a 5-HT1 agonist or antagonist is indicated.

Asymmetric synthesis of arylpropionic acids and aryloxy acids by using lactamides as chiral auxiliaries

Two different dynamic kinetic resolution methods have been applied for the asymmetric synthesis of pharmaceutical arylpropionic acids and aryloxy acids by using amides of (S)-lactic acid as chiral auxiliaries. For arylpropionic acids the esterification mediated by dicyclohexylcarbodiimide (DCC) and 4-(dimethylamino)pyridine (DMAP) proceeds with good asymmetric induction, while for aryloxyacetic acids the keystep is a diastereoselective substitution reaction in the presence of triethylamine and n-hexylammonium iodide as additives. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Enantioselective microbial hydrolysis of dissymmetrical cyclic carbonates with disubstitution

Enantioselective microbial hydrolysis of C1 and C2 dissymmetrical cyclic carbonates with disubstitution (methyl and another groups) has been developed. Pseudomonas diminuta (FU0090), a bacterium, efficiently catalyzes the hydrolysis of five-membered cyclic carbonates. While the trans-substrates are hydrolyzed with low enantioselectivities and/or reactivities, the microbe hydrolyzes the cis-substrates with very high enantioselectivities to afford the corresponding almost optically pure anti-(2R,3S)-diols. On the other hand, six-membered trans-cyclic carbonates are enantioselectively hydrolyzed to afford the corresponding optically active syn-(2R,4R)-diols, although the hydrolysis of the cis-substrates gives racemic compounds. In all cases, the enzyme prefers the (R)-enantiomer for the carbon atom bearing a methyl group.

Optically active antifungal azoles: Synthesis and antifungal activity of (2R,3S)-2-(2,4-difluorophenyl)-3-(5-{2-[4-aryl-piperazin-1-yl]-ethyl} -tetrazol-2-yl/1-yl)-1-[1,2,4]-triazol-1-yl-butan-2-ol

A series of (2R,3S)-2-(2,4-difluorophenyl)-3-(5-{2-[4-aryl-piperazin-1-yl]- ethyl}-tetrazol-2-yl)-1-[1,2,4]-triazol-1-yl-butan-2-ol (11a-n) and (2R,3S)-2-(2,4-difluorophenyl)-3-(5-{2-[4-aryl-piperazin-1-yl]-ethyl} -tetrazole-1-yl)-1-[1,2,4]-triazol-1-yl-butan-2-ol (12a-n) has been synthesized. The antifungal activity of compounds was evaluated by in vitro agar diffusion and broth dilution assay. Compounds 11d and its positional isomer 12d having 3-trifluoromethyl substitution on the phenyl ring of piperazine demonstrated significant antifungal activity against variety of fungal cultures (Candida spp. C. neoformans and Aspergillus spp.). The compound 12d showed MIC value of 0.12μg/mL for C. albicans, C. albicans V-01-191A-261 (resistant strain); 0.25μg/mL for C. tropicalis, C. parapsilosis ATCC 22019 and C. krusei and MIC value of 0.5μg/mL for C. glabrata, C. krusei ATCC 6258, which is comparable to itraconazole and better than fluconazole. Further, compound 11d showed significant activity (MIC; 0.25-0.5μg/mL) against Candida spp. and strong anticryptococcal activity (MIC; 0.25μg/mL) against C. neoformans.

Tricyclic indole-2-carboxylic acids: Highly in vivo active and selective antagonists for the glycine binding site of the NMDA receptor

A series of tricyclic indole-2-carboxylic acid derivatives were synthesized and evaluated by the radioligand binding assay and the anticonvulsant effects in the mouse NMDA-induced seizure model. Among them, derivatives of 3S-(-)-4 such as 3a, 3f, and 3g which had certain zwitterionic anilides showed high affinity to the NMDA-glycine binding site. The absolute configuration of 3S-(-)-4 was confirmed by X-ray crystallographic analysis. In particular, 3g (SM-31900) was found to be a highly active glycine antagonist for both in vitro and in vivo assays (Ki = 1.0 ± 0.1 nM, ED50 = 2.3 mg/kg, iv) and also showed high selectivity for the glycine site. In addition, 3g was soluble enough in aqueous media (> 10 mg/mL at pH 7.4) to use for medications by intravenous injection.

Production of optically active triazole compounds and their intermediates

A compound of the formula (V): STR1 wherein Ar' is a halogenated phenyl group, R is a hydrocarbon residue having a functional group at the α-carbon, R3' is an optionally substituted aliphatic or aromatic hydrocarbon residue or an optionally substituted aromatic heterocyclic group, Y and Z are, the same or different, a nitrogen atom or a methine group optionally substituted with a lower alkyl group, and (R) and (S) represent configurations, which is an optically active intermediate for production of optically active triazole compounds (I): STR2 wherein the symbols have the same meanings as defined above, and methods of preparing the compounds (V) and (I).