(2R,4S)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (2R,4S)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid
• CAS No.: 681128-50-7
• Molecular Formula: C10H16FNO4
• Molecular Weight: 233.23700
• Hs Code.: 2933998090
• European Community (EC) Number: 826-472-5
• DSSTox Substance ID: DTXSID30433145
• Wikidata: Q82247270
• Mol file: 681128-50-7.mol

Synonyms:681128-50-7;(2R,4S)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid;(4S)-1-Boc-4-fluoro-D-proline;(2R,4S)-4-fluoro-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid;(2R,4S)-1-[(tert-butoxy)carbonyl]-4-fluoropyrrolidine-2-carboxylic acid;MFCD08706411;N-Boc-(4S,2R)-4-fluoro-2-pyrrolidinecarboxylic acid;C10H16FNO4;(2r,4s)-1-((tert-butoxy)carbonyl)-4-fluoropyrrolidine-2-carboxylic acid;SCHEMBL1853822;N-Boc-trans-4-fluoro-D-proline;AMY3080;DTXSID30433145;YGWZXQOYEBWUTH-NKWVEPMBSA-N;AKOS015898027;DS-5551;HY-W021482;CS-0040722;EN300-154319;P10646;A867129;(2R,4S)-1-Boc-4-fluoropyrrolidine-2-carboxylic acid;(2R,4S)-1-(Boc)-4-fluoropyrrolidine-2-carboxylic acid;Z1505702390;(2R,4S)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylicacid;(2R,4S)-1-tert-butoxycarbonyl-4-fluoro-pyrrolidine-2-carboxylic acid;(2R,4S)-4-Fluoro-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

Chemical Property of (2R,4S)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid

Chemical Property:

• Boiling Point: 346.0±42.0 °C(Predicted)
• PKA: 3.53±0.40(Predicted)
• PSA: 66.84000
• Density: 1.24±0.1 g/cm3(Predicted)
• LogP: 1.35640
• Storage Temp.: 2-8°C
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 233.10633615
• Heavy Atom Count: 16
• Complexity: 300

Purity/Quality:

≥99% ^*data from raw suppliers

(2R,4S)-1-(tert-Butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(CC1C(=O)O)F
• Isomeric SMILES: CC(C)(C)OC(=O)N1C[C@H](C[C@@H]1C(=O)O)F

Technology Process of (2R,4S)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid

There total 6 articles about (2R,4S)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid 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: 98.1%

di-tert-butyl dicarbonate (24424-99-5) + (2R,4S)-4-fluoropyrrolidine-2-carboxylic acid (913820-71-0) → (2R,4S)-1-(tert- butoxycarbonyl)- 4- fluoropyrrolidine- 2-carboxylic acid (681128-50-7)

Guidance literature:

With water; sodium hydroxide; In tetrahydrofuran; at 0 - 20 ℃; for 8h;

Reference yield:

1-(tert-butyl) 2-methyl (2R,4S)-4-fluoropyrrolidine-1,2-dicarboxylate (647857-39-4) → (2R,4S)-1-(tert- butoxycarbonyl)- 4- fluoropyrrolidine- 2-carboxylic acid (681128-50-7)

Guidance literature:

1-(tert-butyl) 2-methyl (2R,4S)-4-fluoropyrrolidine-1,2-dicarboxylate; With water; sodium hydroxide; In tetrahydrofuran; methanol; for 2h;

With hydrogenchloride; In water; pH=3;

Reference yield:

(2R,4R)-4-hydroxy-2-methoxycarbonylpyrrolidine hydrochloride (114676-59-4) → (2R,4S)-1-(tert- butoxycarbonyl)- 4- fluoropyrrolidine- 2-carboxylic acid (681128-50-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dmap; triethylamine / water; acetone

2.1: (bis-(2-methoxyethyl)amino)sulfur trufluoride / dichloromethane / 12 h / -78 - 20 °C

3.1: sodium hydroxide; water / tetrahydrofuran; methanol / 2 h

3.2: pH 3

With dmap; water; triethylamine; sodium hydroxide; (bis-(2-methoxyethyl)amino)sulfur trufluoride; In tetrahydrofuran; methanol; dichloromethane; water; acetone;

upstream raw materials:

(2R,4R)-4-hydroxy-2-methoxycarbonylpyrrolidine hydrochloride

(2R,4R)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

cis-hydroxy-D-proline

1-(tert-butyl) 2-methyl (2R,4S)-4-fluoropyrrolidine-1,2-dicarboxylate