847805-32-7

Basic information

• Product Name: (S)-4-Boc-2-((S)-hydroxy(phenyl)Methyl)Morpholine
• Synonyms: (S)-4-Boc-2-((S)-hydroxy(phenyl)Methyl)Morpholine;(2S)-2-[(S)-Hydroxyphenylmethyl]-4-morpholinecarboxylic acid 1,1-dimethylethyl ester
• CAS NO: 847805-32-7
• Molecular Formula: C₁₆H₂₃NO₄
• Molecular Weight: 293.35812
• Mol File: 847805-32-7.mol
• Article Data: 9

Chemical Properties

• Melting Point: 104-105℃
• Appearance: /
• CAS DataBase Reference: (S)-4-Boc-2-((S)-hydroxy(phenyl)Methyl)Morpholine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-Boc-2-((S)-hydroxy(phenyl)Methyl)Morpholine(847805-32-7)
• EPA Substance Registry System: (S)-4-Boc-2-((S)-hydroxy(phenyl)Methyl)Morpholine(847805-32-7)

Safety Data

• Hazardous Substances Data: 847805-32-7(Hazardous Substances Data)

Usage

Description

(S)-4-Boc-2-((S)-hydroxy(phenyl)Methyl)Morpholine is a chemical compound belonging to the morpholine family. It features a 2-((S)-hydroxy(phenyl)methyl) group attached to the 4-position of the morpholine ring and a Boc (tert-butoxycarbonyl) protecting group at the nitrogen atom in the 2-position. The (S) designation signifies that the molecule is in its stereochemically pure form, with substituents arranged in a specific spatial configuration. (S)-4-Boc-2-((S)-hydroxy(phenyl)Methyl)Morpholine is crucial for its biological activity and interactions with other molecules.

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 
• 911061-50-2 (2R,3S)-1-bromo-3-phenylpropane-2,3-diol 
• 911061-51-3 C₉H₁₁N₃O₂ 
• 911061-52-4 C₉H₁₃NO₂ 
• 911061-53-5 2-chloro-N-((2S,3S)-2,3-dihydroxy-3-phenylpropyl)acetamide 
• 911061-54-6 C₁₁H₁₃NO₃ 
• 4392-24-9 Cinnamyl bromide 
• 132073-83-7 (S)-morpholin-2-ylmethanol 
• 135065-76-8 tert-butyl (2S)-2-(hydroxymethyl)morpholine-4-carboxylate 
• 847805-30-5 (6S)-6-(hydroxymethyl)morpholin-3-one 
• 847805-29-2 (-)-2-chloro-N-((S)-2,3-dihydroxypropyl)acetamide 

Downstream Products

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

Relevant articles and documents

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.

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.

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