(S)-5-amino-3,3-difluoro-piperidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (S)-5-amino-3,3-difluoro-piperidine-1-carboxylic acid benzyl ester
• CAS No.: 1562988-38-8
• Molecular Formula: C₁₃H₁₆F₂N₂O₂
• Molecular Weight: 270.279
• Mol file: 1562988-38-8.mol

Synonyms:(S)-5-amino-3,3-difluoro-piperidine-1-carboxylic acid benzyl ester

Chemical Property of (S)-5-amino-3,3-difluoro-piperidine-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

≥98% ^*data from raw suppliers

(S)-Benzyl5-amino-3,3-difluoropiperidine-1-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-5-amino-3,3-difluoro-piperidine-1-carboxylic acid benzyl ester

There total 13 articles about (S)-5-amino-3,3-difluoro-piperidine-1-carboxylic acid benzyl ester 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:

benzyl (5S)-5-(tert-butoxycarbonylamino)-3,3-difluoropiperidine-1-carboxylate (1187055-41-9) → (S)-5-amino-3,3-difluoro-piperidine-1-carboxylic acid benzyl ester (1562988-38-8)

Guidance literature:

With hydrogenchloride; In ethyl acetate; at 25 ℃; for 1h;

Reference yield:

cis-hydroxy-D-proline (2584-71-6,30724-02-8) → (S)-5-amino-3,3-difluoro-piperidine-1-carboxylic acid benzyl ester (1562988-38-8)

Guidance literature:

Multi-step reaction with 12 steps

1: thionyl chloride / 16 h / 0 - 60 °C / Inert atmosphere

2: triethylamine / dichloromethane / 16 h / 60 °C / Inert atmosphere

3: triethylamine / dichloromethane / 16 h / 0 - 60 °C

4: lithium borohydride / tetrahydrofuran / 16 h / 0 - 30 °C / Inert atmosphere

5: tetrabutylammoniun azide; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate / dichloromethane / 4.5 h / -78 °C

6: hydrogen / methanol / 2 h / 20 °C / 2068.65 Torr

7: triethylamine / dichloromethane / 16 h / 20 °C

8: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 4.5 h / 25 °C / 2585.81 Torr / Inert atmosphere

9: triethylamine / dichloromethane / 3 h / 25 °C

10: Dess-Martin periodane / dichloromethane / 12 h / 25 °C

11: diethylamino-sulfur trifluoride / dichloromethane / 12 h / 0 - 25 °C / Inert atmosphere

12: hydrogenchloride / ethyl acetate / 1 h / 25 °C

With hydrogenchloride; lithium borohydride; thionyl chloride; diethylamino-sulfur trifluoride; palladium 10% on activated carbon; hydrogen; tetrabutylammoniun azide; Dess-Martin periodane; triethylamine; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;

Reference yield:

(2R,4R)-4-Hydroxy-pyrrolidine-2-carboxylic acid methyl ester (114676-47-0,775275-31-5,790644-51-8,754962-86-2) → (S)-5-amino-3,3-difluoro-piperidine-1-carboxylic acid benzyl ester (1562988-38-8)

Guidance literature:

Multi-step reaction with 11 steps

1: triethylamine / dichloromethane / 16 h / 60 °C / Inert atmosphere

2: triethylamine / dichloromethane / 16 h / 0 - 60 °C

3: lithium borohydride / tetrahydrofuran / 16 h / 0 - 30 °C / Inert atmosphere

4: tetrabutylammoniun azide; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate / dichloromethane / 4.5 h / -78 °C

5: hydrogen / methanol / 2 h / 20 °C / 2068.65 Torr

6: triethylamine / dichloromethane / 16 h / 20 °C

7: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 4.5 h / 25 °C / 2585.81 Torr / Inert atmosphere

8: triethylamine / dichloromethane / 3 h / 25 °C

9: Dess-Martin periodane / dichloromethane / 12 h / 25 °C

10: diethylamino-sulfur trifluoride / dichloromethane / 12 h / 0 - 25 °C / Inert atmosphere

11: hydrogenchloride / ethyl acetate / 1 h / 25 °C

With hydrogenchloride; lithium borohydride; diethylamino-sulfur trifluoride; palladium 10% on activated carbon; hydrogen; tetrabutylammoniun azide; Dess-Martin periodane; triethylamine; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;

upstream raw materials:

cis-hydroxy-D-proline

(2R,4R)-4-Hydroxy-pyrrolidine-2-carboxylic acid methyl ester

(2R,4R)-methyl 1-benzyl-4-hydroxypyrrolidine-2-carboxylate

methyl (2R,4R)-1-benzyl-4-[tert-butyl(dimethyl)silyl]oxy-pyrrolidine-2-carboxylate

Refernces