(R)-1-(tert-Butoxycarbonyl)-2-(4-fluorobenzyl)pyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (R)-1-(tert-Butoxycarbonyl)-2-(4-fluorobenzyl)pyrrolidine-2-carboxylic acid
• CAS No.: 706806-64-6
• Molecular Formula: C₁₇H₂₂FNO₄
• Molecular Weight: 323.364
• European Community (EC) Number: 634-731-7
• DSSTox Substance ID: DTXSID80375945
• Nikkaji Number: J1.945.764H
• Wikidata: Q76148964
• Mol file: 706806-64-6.mol

Synonyms:706806-64-6;(R)-1-(tert-Butoxycarbonyl)-2-(4-fluorobenzyl)pyrrolidine-2-carboxylic acid;BOC-(R)-ALPHA-(4-FLUORO-BENZYL)-PROLINE;(2R)-2-[(4-fluorophenyl)methyl]-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid;MFCD06797544;Boc-(R)-alpha-(4-fluorobenzyl)-propline;BOC-(R)-alpha-(4-FLUOROBENZYL)-PROLINE;SCHEMBL2252204;DTXSID80375945;(R)-1-Boc-2-(4-fluorobenzyl)-2-pyrrolidinecarboxylic acid;(R)-1-(tert-Butoxycarbonyl)-2-(4-fluorobenzyl)pyrrolidine-2-carboxylicacid;AKOS015949665;N-Boc-2-(4-fluorobenzyl)-L-proline;PS-12080;1-(tert-Butoxycarbonyl)-2-[(4-fluorophenyl)methyl]-L-proline;Boc-(R)-alpha-(4-fluorobenzyl)-Pro-OH, >=98.0% (HPLC);(2R)-1-(tert-Butoxycarbonyl)-2-(4-fluorobenzyl)-2-pyrrolidinecarboxylic acid;(R)-1-(tert-Butoxycarbonyl)-2-(4-fluorobenzyl)-pyrrolidine-2-carboxylic acid

Chemical Property of (R)-1-(tert-Butoxycarbonyl)-2-(4-fluorobenzyl)pyrrolidine-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 8.69E-09mmHg at 25°C
• Melting Point: 70-72℃
• Refractive Index: 1.543
• Boiling Point: 447.4oC at 760 mmHg
• Flash Point: 224.4oC
• PSA: 66.84000
• Density: 1.242g/cm3
• LogP: 3.16040
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 323.15328635
• Heavy Atom Count: 23
• Complexity: 454

Purity/Quality:

97% ^*data from raw suppliers

Boc-(R)-α-(4-fluorobenzyl)-Pro-OH ≥98.0% (HPLC) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCCC1(CC2=CC=C(C=C2)F)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N1CCC[C@@]1(CC2=CC=C(C=C2)F)C(=O)O

Technology Process of (R)-1-(tert-Butoxycarbonyl)-2-(4-fluorobenzyl)pyrrolidine-2-carboxylic acid

There total 2 articles about (R)-1-(tert-Butoxycarbonyl)-2-(4-fluorobenzyl)pyrrolidine-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: 92.0%

1-(tert-butyl) 2-methyl 2-(4-fluorobenzyl)pyrrolidine-1,2-dicarboxylate → 1-(tert-butoxycarbonyl)-2-(4-fluorobenzyl)pyrrolidine-2-carboxylic acid (351002-78-3,706806-64-6)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; at 60 ℃; for 3h;

DOI:10.1021/acs.joc.1c01133

Reference yield:

(+/-)-N-tert-butoxycarbonylproline methyl ester (145681-01-2) → 1-(tert-butoxycarbonyl)-2-(4-fluorobenzyl)pyrrolidine-2-carboxylic acid (351002-78-3,706806-64-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium hexamethyldisilazane / toluene; tetrahydrofuran / 0.33 h / -78 - 0 °C

1.2: 4-fluorobenzyl halide / 12 h / 20 °C

2.1: sodium hydroxide / tetrahydrofuran; methanol / 3 h / 60 °C

With sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; toluene;

DOI:10.1021/acs.joc.1c01133

upstream raw materials:

(+/-)-N-tert-butoxycarbonylproline methyl ester