158568-64-0

Basic information

• Product Name: 1-Azabicyclo[2.2.2]octan-3-ol, 3-(mercaptomethyl)-, (S)- (9CI)
• Synonyms: (S)-3-(mercaptomethyl)quinuclidin-3-ol;1-Azabicyclo[2.2.2]octan-3-ol, 3-(mercaptomethyl)-, (S)- (9CI);(S)-3-Hydroxy-3-mercaptomethylquinuclidine
• CAS NO: 158568-64-0
• Molecular Formula: C8H15NOS
• Molecular Weight: 173.28
• Mol File: 158568-64-0.mol

Chemical Properties

• Boiling Point: 286.0±15.0 °C(Predicted)
• Appearance: /
• Density: 1.21±0.1 g/cm3(Predicted)
• PKA: 10.18±0.10(Predicted)
• CAS DataBase Reference: 1-Azabicyclo[2.2.2]octan-3-ol, 3-(mercaptomethyl)-, (S)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Azabicyclo[2.2.2]octan-3-ol, 3-(mercaptomethyl)-, (S)- (9CI)(158568-64-0)
• EPA Substance Registry System: 1-Azabicyclo[2.2.2]octan-3-ol, 3-(mercaptomethyl)-, (S)- (9CI)(158568-64-0)

Safety Data

• Hazardous Substances Data: 158568-64-0(Hazardous Substances Data)

Usage

Uses

1-Azabicyclo[2.2.2]octan-3-ol, 3-(mercaptomethyl)-, (S)(9CI) may have a range of applications across different industries, including but not limited to:
Used in Organic Synthesis:
1-Azabicyclo[2.2.2]octan-3-ol, 3-(mercaptomethyl)-, (S)(9CI) is used as a building block or intermediate in organic synthesis for the development of new compounds with specific properties. Its unique structure and thiol functionality make it a valuable component in the synthesis of pharmaceuticals, agrochemicals, or other specialty chemicals.
Used in Pharmaceutical Chemistry:
In the pharmaceutical industry, 1-Azabicyclo[2.2.2]octan-3-ol, 3-(mercaptomethyl)-, (S)(9CI) may be utilized as an active pharmaceutical ingredient (API) or as a key intermediate in the synthesis of APIs. Its chiral nature and thiol group could contribute to the development of enantioselective drugs with improved efficacy and reduced side effects.
Used in Material Science:
1-Azabicyclo[2.2.2]octan-3-ol, 3-(mercaptomethyl)-, (S)(9CI) may also find applications in material science, where its unique structure and properties could be leveraged to create new materials with specific characteristics, such as improved stability, reactivity, or selectivity in various chemical processes.

Upstream product

• 158469-75-1 (S)-3-hydroxy-3-benzylthiomethylquinuclidine 
• 158469-71-7 4-<(2-hydroxy-1-methylene)ethyl>-1-piperidinecarboxylic acid(1,1-dimethylethyl) ester 
• 158469-70-6 4-(2-hydroxy-1-oxoethyl)-1-piperidinecarboxylic acid (1,1-dimethylethyl)ester 
• 158469-73-9 4-<(S)-2-benzylthio-1-hydroxy-1-hydroxymethylethyl>-1-piperidinecarboxylic acid (1,1-dimethylethyl) ester 
• 158469-74-0 4-<(S)-2-benzylthio-1-hydroxy-1-<<(methanesulfonyl)oxy>methyl>ethyl>-1-piperidinecarboxylic acid (1,1-dimethylethyl) ester 
• 64168-68-9 Spiro- Hydrochlorid 
• 1193-65-3 3-quinuclidinone hydrochloride 
• 1435450-21-7 C₉H₁₃NO₂S 
• 1435450-13-7 C₈H₁₄BrNO*BrH 
• 41353-91-7 1’-azaspiro[oxirane-2,3’-bicyclo[2.2.2]octane] 
• 124620-88-8 2-methylspiro(1,3-oxathiolane-5,3'-quinuclidine) 
• 158469-72-8 4-<(S)-2-hydroxymethyl-2-oxiranyl>-1-piperidinecarboxylic acid (1,1-dimethylethyl) ester 

Downstream Products

• 107220-27-9 trans-cevimeline 
• 107220-27-9 cevimeline 
• 173553-37-2 Cevimeline hydrochloride 

Relevant articles and documents

A new route to cevimeline

The present work demonstrates a new route for the synthesis of cevimeline in which safe and odorless thiourea is utilized as a thiolating reagent.

PROCESS FOR THE PREPARATION OF CIS-2-METHYLSPIRO (1, 3-OXATHIOLANE 5-3') QUINUCLIDINE

Methods are provided for making pharmaceutical-grade cis-2-methylspiro(1,3-oxathiolane-5,3′)quinuclidine and pharmaceutically acceptable salts thereof by isomerizing racemic 2-methylspiro(1,3-oxathiolane-5,3′)quinuclidine to cis-2-methylspiro(1,3-oxathiolane-5,3′)quinuclidine and subsequent purification of the C-MSOQ by salt formation with inexpensive and commercially available material such as sulfuric acid. Purification methods are disclosed which employ an organic solvent/water system and recrystallization with an organic solvent such as acetone.

Method for producing 2-methylspiro(1,3-oxathiolane-5,3')quinuclidine

A method for producing 2-methylspiro(1,3-oxathiolane-5,3')quinuclidine, which comprises reacting 3-hydroxy-3-mercaptomethylquinuclidine or a salt thereof and a carbonyl compound in the presence of a catalyst made of at least one member selected from the group consisting of tin halides, oxyacids of phosphorus, phosphorus oxyhalides and organic sulfonic acids, to produce cis-form 2-methylspiro(1,3-oxathiolane-5,3')quinuclidine or a salt thereof.

EPC-Synthesis of (S)-3-Hydroxy-3-mercaptomethylquinuclidine, a Chiral Building Block for the Synthesis of the Muscarinic Agonist AF 102B

The catalytic modification of the Sharpless-epoxidation reaction was employed in a short EPC-synthesis of the title compound.The asymmetric epoxidation of the allylic alcohol (6) proceeded in 75percent yield and 94percent enantiomeric excess.In a 4 step s