(3S,7S)-1-aza-3-benzyl-3-methyl-4-thiabicyclo[5.3.0]-2-decanone

Base Information

• Chemical Name: (3S,7S)-1-aza-3-benzyl-3-methyl-4-thiabicyclo[5.3.0]-2-decanone
• CAS No.: 335203-32-2
• Molecular Formula: C₁₆H₂₁NOS
• Molecular Weight: 275.415
• Mol file: 335203-32-2.mol

Synonyms:(3S,7S)-1-aza-3-benzyl-3-methyl-4-thiabicyclo[5.3.0]-2-decanone

Chemical Property of (3S,7S)-1-aza-3-benzyl-3-methyl-4-thiabicyclo[5.3.0]-2-decanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,7S)-1-aza-3-benzyl-3-methyl-4-thiabicyclo[5.3.0]-2-decanone

There total 7 articles about (3S,7S)-1-aza-3-benzyl-3-methyl-4-thiabicyclo[5.3.0]-2-decanone 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:

(7S)-1-aza-4-thiabicyclo[5.3.0]-2-decanone (335203-22-0) → (3S,7S)-1-aza-3-benzyl-3-methyl-4-thiabicyclo[5.3.0]-2-decanone (335203-32-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium diisopropylamide; lithium chloride / cooling

1.2: 90 percent / 3 h / -78 °C

2.1: lithium diisopropylamide; lithium chloride / cooling

2.2: 3 h / -78 °C

With lithium chloride; lithium diisopropyl amide;

DOI:10.1021/ol0364428

Reference yield:

((S)-2-Pyrrolidin-2-yl-ethylsulfanyl)-acetic acid → (3S,7S)-1-aza-3-benzyl-3-methyl-4-thiabicyclo[5.3.0]-2-decanone (335203-32-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.92 g / 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide; hydroxybenzotriazole; triethylamine / CH₂Cl₂ / 24 h / 23 °C

2: 90 percent / LDA; lithium chloride / tetrahydrofuran; hexane / 3 h / -78 °C

3: 88 percent / LDA; LiCl / tetrahydrofuran; hexane / 2.5 h / -78 °C

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/ja0058280

Reference yield:

2-(2-methoxycarbonylmethylsulfanyl-ethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (335203-56-0) → (3S,7S)-1-aza-3-benzyl-3-methyl-4-thiabicyclo[5.3.0]-2-decanone (335203-32-2)

Guidance literature:

Multi-step reaction with 5 steps

1: LiOH*H₂O / tetrahydrofuran; H₂O / 5.5 h / 23 °C

2: trifluoroacetic acid / 0.5 h / 23 °C

3: 1.92 g / 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide; hydroxybenzotriazole; triethylamine / CH₂Cl₂ / 24 h / 23 °C

4: 90 percent / LDA; lithium chloride / tetrahydrofuran; hexane / 3 h / -78 °C

5: 88 percent / LDA; LiCl / tetrahydrofuran; hexane / 2.5 h / -78 °C

With lithium hydroxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; trifluoroacetic acid; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; water;

DOI:10.1021/ja0058280

upstream raw materials:

(3R,7S)-1-aza-3-benzyl-4-thiabicyclo[5.3.0]-2-decanone

methyl iodide

benzyl bromide

(7S)-1-aza-4-thiabicyclo[5.3.0]-2-decanone