(S)-3-(mercaptomethyl)quinuclidin-3-ol

Base Information

• Chemical Name: (S)-3-(mercaptomethyl)quinuclidin-3-ol
• CAS No.: 158568-64-0
• Molecular Formula: C₈H₁₅NOS
• Molecular Weight: 173.279
• DSSTox Substance ID: DTXSID10576206
• Wikidata: Q82465774
• Mol file: 158568-64-0.mol

Synonyms:(S)-3-(mercaptomethyl)quinuclidin-3-ol;158568-64-0;(3S)-3-(Sulfanylmethyl)-1-azabicyclo[2.2.2]octan-3-ol;1-Azabicyclo[2.2.2]octan-3-ol, 3-(mercaptomethyl)-, (S)- (9CI);(S)-3-Hydroxy-3-mercaptomethylquinuclidine;DTXSID10576206;AKOS006307049;AKOS016004151

Chemical Property of (S)-3-(mercaptomethyl)quinuclidin-3-ol

Chemical Property:

• Boiling Point: 286.0±15.0 °C(Predicted)
• PKA: 10.18±0.10(Predicted)
• PSA: 62.27000
• Density: 1.21±0.1 g/cm3(Predicted)
• LogP: 0.31080
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 173.08743528
• Heavy Atom Count: 11
• Complexity: 156

Purity/Quality:

(S)-3-(Mercaptomethyl)quinuclidin-3-ol 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN2CCC1C(C2)(CS)O
• Isomeric SMILES: C1CN2CCC1[C@](C2)(CS)O

Technology Process of (S)-3-(mercaptomethyl)quinuclidin-3-ol

There total 14 articles about (S)-3-(mercaptomethyl)quinuclidin-3-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 50.0%

Spiro- Hydrochlorid (64168-68-9) → 3-hydroxy-3-(mercaptomethyl)quinuclidine (107220-26-8,158568-64-0)

Guidance literature:

With hydrogen sulfide; sodium hydroxide; In water; at 45 ℃; for 2.5h;

DOI:10.1016/j.tetlet.2013.03.090

Reference yield: 46.0%

(S)-3-hydroxy-3-benzylthiomethylquinuclidine (158469-75-1) → (S)-3-hydroxy-3-mercaptomethylquinuclidine (158568-64-0)

Guidance literature:

With calcium hexammine; In diethyl ether; for 5h; Ambient temperature;

Reference yield:

1’-azaspiro[oxirane-2,3’-bicyclo[2.2.2]octane] (41353-91-7) → 3-hydroxy-3-(mercaptomethyl)quinuclidine (107220-26-8,158568-64-0)

Guidance literature:

With hydrogen sulfide; In methanol; dichloromethane; at 0 - 5 ℃;

upstream raw materials:

(S)-3-hydroxy-3-benzylthiomethylquinuclidine

4-<(2-hydroxy-1-methylene)ethyl>-1-piperidinecarboxylic acid(1,1-dimethylethyl) ester

4-(2-hydroxy-1-oxoethyl)-1-piperidinecarboxylic acid (1,1-dimethylethyl)ester

4-<(S)-2-benzylthio-1-hydroxy-1-hydroxymethylethyl>-1-piperidinecarboxylic acid (1,1-dimethylethyl) ester

Downstream raw materials:

trans-cevimeline

cevimeline

Cevimeline hydrochloride