((3S,5R)-3-amino-5-fluoropiperidin-1-yl)(2-methoxyphenyl)methanone

Base Information

• Chemical Name: ((3S,5R)-3-amino-5-fluoropiperidin-1-yl)(2-methoxyphenyl)methanone
• CAS No.: 1611488-81-3
• Molecular Formula: C₁₃H₁₇FN₂O₂
• Molecular Weight: 252.289
• Mol file: 1611488-81-3.mol

Synonyms:((3S,5R)-3-amino-5-fluoropiperidin-1-yl)(2-methoxyphenyl)methanone

Chemical Property of ((3S,5R)-3-amino-5-fluoropiperidin-1-yl)(2-methoxyphenyl)methanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((3S,5R)-3-amino-5-fluoropiperidin-1-yl)(2-methoxyphenyl)methanone

There total 14 articles about ((3S,5R)-3-amino-5-fluoropiperidin-1-yl)(2-methoxyphenyl)methanone 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: 42.0%

C18H25FN2O4 → ((3S,5R)-3-amino-5-fluoropiperidin-1-yl)(2-methoxyphenyl)methanone (1611488-81-3)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; water; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1002/chem.201302423

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → ((3S,5R)-3-amino-5-fluoropiperidin-1-yl)(2-methoxyphenyl)methanone (1611488-81-3)

Guidance literature:

Multi-step reaction with 9 steps

1: triethylamine / dichloromethane / 8 h / Inert atmosphere; Reflux

2: triethylamine / dichloromethane / 14 h / 0 - 20 °C / Inert atmosphere

3: sodium azide / N,N-dimethyl-formamide / 8 h / 65 °C / Inert atmosphere

4: lithium aluminium tetrahydride / tetrahydrofuran / 3.5 h / 0 - 20 °C / Inert atmosphere

5: 1,4-dioxane / 20 h / 20 °C / Inert atmosphere

6: diethylamino-sulfur trifluoride / tetrahydrofuran / 13 h / 0 - 20 °C / Inert atmosphere

7: palladium 10% on activated carbon; formic acid; piperidine / tetrahydrofuran / Microwave irradiation

8: triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere

9: hydrogenchloride / water; 1,4-dioxane / 2 h / 20 °C / Inert atmosphere

With piperidine; hydrogenchloride; lithium aluminium tetrahydride; formic acid; sodium azide; diethylamino-sulfur trifluoride; palladium 10% on activated carbon; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/chem.201302423

Reference yield:

4R-4-hydroxyproline (51-35-4,30724-02-8) → ((3S,5R)-3-amino-5-fluoropiperidin-1-yl)(2-methoxyphenyl)methanone (1611488-81-3)

Guidance literature:

Multi-step reaction with 10 steps

1: thionyl chloride / 24 h / 0 °C / Inert atmosphere; Reflux

2: triethylamine / dichloromethane / 8 h / Inert atmosphere; Reflux

3: triethylamine / dichloromethane / 14 h / 0 - 20 °C / Inert atmosphere

4: sodium azide / N,N-dimethyl-formamide / 8 h / 65 °C / Inert atmosphere

5: lithium aluminium tetrahydride / tetrahydrofuran / 3.5 h / 0 - 20 °C / Inert atmosphere

6: 1,4-dioxane / 20 h / 20 °C / Inert atmosphere

7: diethylamino-sulfur trifluoride / tetrahydrofuran / 13 h / 0 - 20 °C / Inert atmosphere

8: palladium 10% on activated carbon; formic acid; piperidine / tetrahydrofuran / Microwave irradiation

9: triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere

10: hydrogenchloride / water; 1,4-dioxane / 2 h / 20 °C / Inert atmosphere

With piperidine; hydrogenchloride; lithium aluminium tetrahydride; formic acid; thionyl chloride; sodium azide; diethylamino-sulfur trifluoride; palladium 10% on activated carbon; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/chem.201302423

upstream raw materials:

4R-4-hydroxyproline

methyl (2S,4R)-4-hydroxy-1-[(4-methoxyphenyl)methyl]pyrrolidine-2-carboxylate

L-4-hydroxyproline methyl ester hydrochloride

(2S,4S)-methyl 4-azido-1-tritylpyrrolidine-2-carboxylate

Refernces