rel-(3r,4r)-3-(boc-amino)-5-fluoropiperidine

Base Information

• Chemical Name: rel-(3r,4r)-3-(boc-amino)-5-fluoropiperidine
• CAS No.: 1363378-07-7
• Molecular Formula: C10H19FN2O2
• Molecular Weight: 218.271
• Mol file: 1363378-07-7.mol

Synonyms:rel-(3r,4r)-3-(boc-amino)-5-fluoropiperidine;tert-Butyl ((3R,5R)-5-fluoropiperidin-3-yl)carbamate

Chemical Property of rel-(3r,4r)-3-(boc-amino)-5-fluoropiperidine

Chemical Property:

• Boiling Point: 313.3±42.0 °C(Predicted)
• PKA: 11.68±0.40(Predicted)
• PSA: 50.36000
• Density: 1.08±0.1 g/cm3(Predicted)
• LogP: 1.93080

Purity/Quality:

97% ^*data from raw suppliers

(3R,4R)-rel-3-(Boc-amino)-5-fluoropiperidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (3R,4R)-rel-3-(Boc-amino)-5-fluoropiperidine is a useful reagent for the preparation of FLT3 kinase inhibitor for treating FLT3 mediated diseases.

Technology Process of rel-(3r,4r)-3-(boc-amino)-5-fluoropiperidine

There total 9 articles about rel-(3r,4r)-3-(boc-amino)-5-fluoropiperidine 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: 72.0%

tert-butyl (3R,5R)-5-fluoro-1-tritylpiperidin-3-ylcarbamate → tert-butyl ((3R,5R)-5-fluoropiperidin-3 -yl)carbamate (1363378-07-7,1593969-81-3)

Guidance literature:

With hydrogenchloride; In ethanol; water; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1002/chem.201302423

Reference yield:

(2S,4S)-methyl 4-hydroxy-1-tritylpyrrolidine-2-carboxylate (129430-93-9) → tert-butyl ((3R,5R)-5-fluoropiperidin-3 -yl)carbamate (1363378-07-7,1593969-81-3)

Guidance literature:

Multi-step reaction with 6 steps

1: triethylamine / dichloromethane / 15 h / 0 - 20 °C / Inert atmosphere

2: tetrabutylammoniun azide / acetonitrile / 24 h / 70 °C / Inert atmosphere

3: lithium aluminium tetrahydride / tetrahydrofuran / 2.5 h / 0 - 20 °C / Inert atmosphere

4: 1,4-dioxane / 14 h / 20 °C / Inert atmosphere

5: diethylamino-sulfur trifluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

6: hydrogenchloride / water; ethanol / 1 h / 20 °C / Inert atmosphere

With hydrogenchloride; lithium aluminium tetrahydride; diethylamino-sulfur trifluoride; tetrabutylammoniun azide; triethylamine; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; acetonitrile;

DOI:10.1002/chem.201302423

Reference yield:

hydroxy L-proline (618-27-9,30724-02-8) → tert-butyl ((3R,5R)-5-fluoropiperidin-3 -yl)carbamate (1363378-07-7,1593969-81-3)

Guidance literature:

Multi-step reaction with 8 steps

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

2: triethylamine / chloroform / 27 h / 0 - 20 °C / Inert atmosphere

3: triethylamine / dichloromethane / 15 h / 0 - 20 °C / Inert atmosphere

4: tetrabutylammoniun azide / acetonitrile / 24 h / 70 °C / Inert atmosphere

5: lithium aluminium tetrahydride / tetrahydrofuran / 2.5 h / 0 - 20 °C / Inert atmosphere

6: 1,4-dioxane / 14 h / 20 °C / Inert atmosphere

7: diethylamino-sulfur trifluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

8: hydrogenchloride / water; ethanol / 1 h / 20 °C / Inert atmosphere

With hydrogenchloride; lithium aluminium tetrahydride; thionyl chloride; diethylamino-sulfur trifluoride; tetrabutylammoniun azide; triethylamine; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; chloroform; water; acetonitrile;

DOI:10.1002/chem.201302423

upstream raw materials:

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

hydroxy L-proline

cis-L-hydroxyproline methyl ester

di-tert-butyl dicarbonate

Downstream raw materials:

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