tert-Butyl cis-3-fluoro-4-hydroxypyrrolidine-1-carboxylate

Base Information

• Chemical Name: tert-Butyl cis-3-fluoro-4-hydroxypyrrolidine-1-carboxylate
• CAS No.: 1174020-49-5
• Molecular Formula: C₉H₁₆FNO₃
• Molecular Weight: 205.229
• Hs Code.: 2933998090
• Mol file: 1174020-49-5.mol

Synonyms:

Chemical Property of tert-Butyl cis-3-fluoro-4-hydroxypyrrolidine-1-carboxylate

Chemical Property:

• Boiling Point: 282.3±40.0 °C(Predicted)
• PKA: 13.54±0.40(Predicted)
• Density: 1.18±0.1 g/cm3(Predicted)

Purity/Quality:

98%,99%, ^*data from raw suppliers

(3R,4S)-1-Boc-3-fluoro-4-hydroxypyrrolidine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl cis-3-fluoro-4-hydroxypyrrolidine-1-carboxylate

There total 7 articles about tert-Butyl cis-3-fluoro-4-hydroxypyrrolidine-1-carboxylate 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: 71.6%

1-tert-butoxycarbonyl-3,4-epoxypyrrolidine (114214-49-2) → 3-hydroxy-4-fluoro-N-tert-butoxycarbonylpyrrolidine (1379325-25-3,1174020-49-5,1174020-51-9,2055223-76-0,1174020-50-8,1174020-48-4)

Guidance literature:

With triethylamine tris(hydrogen fluoride); at 100 ℃;

Reference yield: 45.0%

1-tert-butoxycarbonyl-3,4-epoxypyrrolidine (114214-49-2) → trans-tert-butyl 3-fluoro-4-hydroxypyrrolidine-1-carboxylate (1174020-49-5,1174020-51-9,2055223-76-0,1174020-50-8,1174020-48-4)

Guidance literature:

With triethylamine hydrofluoride;

DOI:10.1016/j.bmcl.2005.07.026

Reference yield: 43.9%

[4-[(3S,4R)-1-tert-butoxycarbonyl-4-fluoropyrrolidin-3-yl]oxycarbonylphenyl]azinate → cis-tert-butyl 3-fluoro-4-hydroxypyrrolidine-1-carboxylate (1174020-49-5,1174020-51-9,2055223-76-0,1174020-50-8,1174020-48-4)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 0 ℃; for 2h;

upstream raw materials:

1-tert-butoxycarbonyl-3,4-epoxypyrrolidine

N-(tert-butoxycarbonyl)-3-pyrroline

tert-butyl diallylcarbamate

Downstream raw materials:

3-hydroxy-4-fluoropyrrolidine

(3S,4R)-4-fluoropyrrolidin-3-ol

(3S,4S)-4-fluoropyrrolidin-3-ol

tert-butyl 3-fluoro-4-oxopyrrolidine-1-carboxylate

Refernces

• 1、 -. "(HETERO)ARYLAMIDE COMPOUND FOR INHIBITING PROTEIN KINASE ACTIVITY". Paragraph 0164-0165. . Retrieved 2019/10/29.
• 2、 -. "1 -OXO-1,2-DIHYDROISOQUINOLIN-7-YL-(5-SUBSTITUTED-THIOPHEN-2-YL)-SULFONAMIDE COMPOUNDS, FORMULATIONS CONTAINING THOSE COMPOUNDS, AND THEIR USE AS AICARFT INHIBITORS IN THE TREATMENT OF CANCERS". Page/Page column 25. . Retrieved 2016/06/28.