847805-32-7

Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-4-Boc-2-((S)-hydroxy(phenyl)Methyl)Morpholine is used as an intermediate in the pharmaceutical industry for the synthesis of various pharmaceuticals and organic compounds. Its unique structure and stereochemistry make it a valuable component in the development of new drugs and therapeutic agents.
Used in Organic Chemistry:
In the field of organic chemistry, (S)-4-Boc-2-((S)-hydroxy(phenyl)Methyl)Morpholine serves as a key intermediate for the synthesis of complex organic molecules. Its specific stereochemistry and functional groups enable chemists to create a wide range of compounds with diverse applications, including those in materials science, agrochemicals, and specialty chemicals.
Used in Research and Development:
(S)-4-Boc-2-((S)-hydroxy(phenyl)Methyl)Morpholine is also utilized in research and development settings, where its unique properties and reactivity are explored for potential applications in various scientific and industrial fields. Its stereochemistry and functional groups make it an interesting candidate for studying molecular interactions and developing new synthetic methodologies.

Upstream product

• 108-86-1 bromobenzene 
• 847805-31-6 (S)-(+)-2-formylmorpholine-4-carboxylic acid tert-butyl ester 
• 911061-55-7 C₁₁H₁₅NO₂ 
• 24424-99-5 di-tert-butyl dicarbonate 
• 100-58-3 phenylmagnesium bromide 
• 133187-21-0 Methyl (S)-(+)-α-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-α-phenylacetate 
• 17199-29-0 (S)-Mandelic acid 
• 133187-22-1 (2S)-2-(tert-butyldimethylsilyloxy)-2-phenylacetaldehyde 
• 1239893-05-0 C₂₃H₂₉NO₄ 
• 869088-59-5 tert-butyl (2S)-2-benzoylmorpholine-4-carboxylate 
• 847805-29-2 (-)-2-chloro-N-((S)-2,3-dihydroxypropyl)acetamide 
• 847805-30-5 (6S)-6-(hydroxymethyl)morpholin-3-one 
• 135065-76-8 tert-butyl (2S)-2-(hydroxymethyl)morpholine-4-carboxylate 
• 132073-83-7 (S)-morpholin-2-ylmethanol 

Downstream Products

• 847805-34-9 (+)-(2S,3S)-2-[α-(2-ethoxyphenoxy)phenylmethyl]morpholine-4-carboxylic acid tert-butyl ester 
• 1097104-02-3 (2S,3S)-N-tert-butoxycarbonyl-2-[α-(2-methylphenoxy)phenylmethyl]morpholine 
• 71620-89-8 (S,S)-reboxetine 
• 1016544-97-0 C₁₆H₂₂BrNO₃ 
• 869088-61-9 tert-butyl (2S)-2-[(S)-(4-chloro-2-methoxyphenoxy)(phenyl)methyl]morpholine-4-carboxylate 

Relevant academic research and scientific papers

Stereodivergent synthesis of all the four stereoisomers of antidepressant reboxetine

Chiral amino alcohol-copper(ii) catalysts Cu-L1c and Cu-ent-L1c were utilized to promote the diastereoselective nitroaldol reactions of chiral aldehydes (S)-3 or (R)-3 with nitromethane, which respectively led to the preferential formation of certain stereoisomer for nitro diol derivatives 4. Using this catalytic protocol, all the four stereoisomers of the antidepressant reboxetine were divergently prepared. The highest overall yield of this synthetic route reached up to 30.5% from aldehyde (S)-3.

Co(iii)(salen)-catalyzed HKR of two stereocentered alkoxy- and azido epoxides: A concise enantioselective synthesis of (S,S)-reboxetine and (+)-epi-cytoxazone

The HKR of racemic syn- or anti- alkoxy- and azido epoxides catalyzed by Co(salen) complex affords a practical access to a series of enantioenriched syn- or anti- alkoxy- and azido epoxides and the corresponding 1,2-diols. This strategy has been successfully employed in the concise, enantioselective synthesis of bioactive molecules such as (S,S)-reboxetine and (+)-epi-cytoxazone.

Design and synthesis of reboxetine analogs morpholine derivatives as selective norepinephrine reuptake inhibitors

As part of a discovery effort aimed at identifying novel norepinephrine reuptake inhibitors (NRIs), a number of substituted morpholines were designed and synthesized. The target compounds contain vicinal stereogenic centers, and the program was greatly facilitated by the adoption of efficient synthetic routes which allowed for the late stage incorporation of structural and physicochemical diversity into the targets. Structure-activity relationships were developed by optimizing individual ring components of the structure for NRI potency and for selectivity against other monoamine reuptake transporters. Several novel morpholine derivatives with a potent and selective NRI profile are described.

Design and synthesis of morpholine derivatives. SAR for dual serotonin & noradrenaline reuptake inhibition

Single enantiomer (SS) and (RR) 2-[(phenoxy)(phenyl)methyl]morpholine derivatives 5, 8-23 are inhibitors of monoamine reuptake. Target compounds were prepared using an enantioselective synthesis employing a highly specific enzyme-catalysed resolution of racemic n-butyl 4-benzylmorpholine-2-carboxylate (26) as the key step. Structure-activity relationships established that serotonin and noradrenaline reuptake inhibition are functions of stereochemistry and aryl/aryloxy ring substitution. Consequently, selective SRI, selective NRI and dual SNRIs were all identified. One of these compounds, a potent and selective dual SNRI, (SS)-5a was selected as a candidate for further pre-clinical evaluation.

Development of SPECT imaging agents for the norepinephrine transporters: [123I]INER

A series of reboxetine analogs was synthesized and evaluated for in vitro binding as racemic mixtures. The best candidate (INER) was synthesized as the optically pure (S,S) enantiomer, labeled with iodine-123 and its in vivo binding determined by SPECT im

NOREPINEPHRINE TRANSPORTER RADIOTRACERS AND METHODS OF SYNTHESES THEREOF

The present invention provides compounds and radiotracers thereof for locating, diagnosing, identifying, evaluating, detecting or quantitating NET by in vivo imaging. The invention also provides methods for locating, diagnosing, identifying, evaluating, detecting or quantitating NET, using radiotracers of high-affinity or labeled compounds of the invention, which exhibit low toxicity, can cross the blood-brain barrier and, preferably, distinguish among normal and abnormal brains. For example, a radiotracer of the invention can be administered to a patient in an amount suitable for in vivo imaging thereof. Preferably, radiotracers of the invention can also be used to locate, diagnosis, identify, evaluate, detect and quantitate NET in such diseases, disorders, conditions or maladies as, without limitation, depression, anxiety, ADHD and drug dependency.

Enantioselective synthesis of (+)-(S,S)-reboxetine

An efficient enantioselective synthesis leading directly to (+)-(S,S)-reboxetine has been described from commercially available trans-cinnammyl bromide using Sharpless asymmetric dihydroxylation as the key step. Georg Thieme Verlag Stuttgart.

Novel compounds

The present invention provides compounds of Formula I wherein R1, R2, R3, and n have any of the values defined in the specification, and pharmaceutically acceptable salts thereof, that are useful as agents in the treatment

Asymmetric synthesis of (+)-(S,S)-reboxetine via a new (S)-2- (hydroxymethyl)morpholine preparation

(Chemical Equation Presented) (S,S)-Reboxetine was synthesized stereospecifically in 30% overall yield and 99% ee in eight steps. Key steps were selective oxidation of an N-protected hydroxymethylmorpholine and aryl-chromium-mediated aromatic nucleophilic substitution.