(R)-(5-amino-3,3-difluoropiperidin-1-yl)(phenyl)methanone

Base Information

• Chemical Name: (R)-(5-amino-3,3-difluoropiperidin-1-yl)(phenyl)methanone
• CAS No.: 1611481-26-5
• Molecular Formula: C₁₂H₁₄F₂N₂O
• Molecular Weight: 240.253
• Mol file: 1611481-26-5.mol

Synonyms:

Chemical Property of (R)-(5-amino-3,3-difluoropiperidin-1-yl)(phenyl)methanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-(5-amino-3,3-difluoropiperidin-1-yl)(phenyl)methanone

There total 12 articles about (R)-(5-amino-3,3-difluoropiperidin-1-yl)(phenyl)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:

C17H22F2N2O3 → (R)-(5-amino-3,3-difluoropiperidin-1-yl)(phenyl)methanone (1611481-26-5)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; water; at 0 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1002/chem.201302423

Reference yield:

trans-4-hydroxyproline (3398-22-9,30724-02-8) → (R)-(5-amino-3,3-difluoropiperidin-1-yl)(phenyl)methanone (1611481-26-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: thionyl chloride / 77 h / 0 - 20 °C / Inert atmosphere; Reflux

2.1: triethylamine / dichloromethane / 5.25 h / 0 °C / Inert atmosphere; Reflux

3.1: triethylamine / dichloromethane / 14 h / 0 °C / Inert atmosphere

4.1: tetrabutylammoniun azide / acetonitrile / 1 h / 70 °C / Inert atmosphere

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

6.1: 1,4-dioxane / 20 h / 20 °C / Inert atmosphere

7.1: triethylamine; trifluoroacetic anhydride / tetrahydrofuran / 8 h / 0 - 100 °C / Inert atmosphere; Microwave irradiation

7.2: 1 h / 20 °C / Inert atmosphere; Microwave irradiation

8.1: palladium 10% on activated carbon; hydrogen / methanol / 12 h / 20 °C / Inert atmosphere

9.1: triethylamine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 6 h / 0 - 20 °C / Inert atmosphere

11.1: diethylamino-sulfur trifluoride / dichloromethane / 17 h / 0 - 20 °C / Inert atmosphere

12.1: hydrogenchloride / water; 1,4-dioxane / 2 h / 0 - 20 °C / Inert atmosphere

With hydrogenchloride; lithium aluminium tetrahydride; thionyl chloride; diethylamino-sulfur trifluoride; palladium 10% on activated carbon; hydrogen; tetrabutylammoniun azide; triethylamine; trifluoroacetic anhydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; acetonitrile;

DOI:10.1002/chem.201302423

Reference yield:

methyl (2R,4S)-4-hydroxypyrrolidine-2-carboxylate (178962-09-9,775275-31-5,790644-51-8,754962-86-2) → (R)-(5-amino-3,3-difluoropiperidin-1-yl)(phenyl)methanone (1611481-26-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: triethylamine / dichloromethane / 5.25 h / 0 °C / Inert atmosphere; Reflux

2.1: triethylamine / dichloromethane / 14 h / 0 °C / Inert atmosphere

3.1: tetrabutylammoniun azide / acetonitrile / 1 h / 70 °C / Inert atmosphere

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

5.1: 1,4-dioxane / 20 h / 20 °C / Inert atmosphere

6.1: triethylamine; trifluoroacetic anhydride / tetrahydrofuran / 8 h / 0 - 100 °C / Inert atmosphere; Microwave irradiation

6.2: 1 h / 20 °C / Inert atmosphere; Microwave irradiation

7.1: palladium 10% on activated carbon; hydrogen / methanol / 12 h / 20 °C / Inert atmosphere

8.1: triethylamine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

9.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 6 h / 0 - 20 °C / Inert atmosphere

10.1: diethylamino-sulfur trifluoride / dichloromethane / 17 h / 0 - 20 °C / Inert atmosphere

11.1: hydrogenchloride / water; 1,4-dioxane / 2 h / 0 - 20 °C / Inert atmosphere

With hydrogenchloride; lithium aluminium tetrahydride; diethylamino-sulfur trifluoride; palladium 10% on activated carbon; hydrogen; tetrabutylammoniun azide; triethylamine; trifluoroacetic anhydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; acetonitrile;

DOI:10.1002/chem.201302423

upstream raw materials:

trans-4-hydroxyproline

methyl (2R,4S)-4-hydroxypyrrolidine-2-carboxylate

(2R,4R)-1-benzyl-2-carbomethoxy-4-<(methylsulfonyl)oxy>pyrrolidine

(2R,4R)-(4-amino-1-benzylpyrrolidin-2-yl)methanol

Refernces