Boc-(R)-alpha-benzyl-proline

Base Information

• Chemical Name: Boc-(R)-alpha-benzyl-proline
• CAS No.: 706806-60-2
• Molecular Formula: C17H23 N O4
• Molecular Weight: 305.374
• DSSTox Substance ID: DTXSID70375939
• Nikkaji Number: J1.945.758C
• Wikidata: Q72442918
• Mol file: 706806-60-2.mol

Synonyms:706806-60-2;Boc-(R)-alpha-benzyl-proline;(R)-2-Benzyl-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid;(2R)-2-benzyl-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid;MFCD06795522;2-Benzyl-N-Boc-L-proline;SCHEMBL194209;DTXSID70375939;JUUNPRGYFCIXSM-QGZVFWFLSA-N;Boc-(R)- alpha -benzyl-Pro-OH;(R)-2-Benzyl-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylicacid;AMY24118;(R)-2-benzyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester;AKOS015948915;DS-4092;C76254;(R)-2-Benzyl-1-Boc-pyrrolidine-2-carboxylic acid;(2R)-1-(tert-Butoxycarbonyl)-2-benzyl-2-pyrrolidinecarboxylic acid

Chemical Property of Boc-(R)-alpha-benzyl-proline

Chemical Property:

• Vapor Pressure: 1.25E-08mmHg at 25°C
• Melting Point: 154-156℃
• Refractive Index: 1.553
• Boiling Point: 443.1oC at 760 mmHg
• Flash Point: 221.8oC
• PSA: 66.84000
• Density: 1.193g/cm3
• LogP: 3.02130
• Storage Temp.: 2-8°C
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 305.16270821
• Heavy Atom Count: 22
• Complexity: 423

Purity/Quality:

98.5% ^*data from raw suppliers

2-Benzyl-N-Boc-L-proline ^*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=CC=C2)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N1CCC[C@@]1(CC2=CC=CC=C2)C(=O)O

Technology Process of Boc-(R)-alpha-benzyl-proline

There total 4 articles about Boc-(R)-alpha-benzyl-proline 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: 41.0%

di-tert-butyl dicarbonate (24424-99-5) + (R)-2-benzylpyrrolidine-2-carboxylic acid (86116-84-9,637020-57-6) → (R)-2-benzyl-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (706806-60-2)

Guidance literature:

(R)-2-benzylpyrrolidine-2-carboxylic acid; With tetramethyl ammoniumhydroxide; In acetonitrile; for 1.5h;

di-tert-butyl dicarbonate; In acetonitrile; for 72h;

Reference yield:

(2R,5R)-5-benzyl-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one (220200-89-5) → (R)-2-benzyl-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (706806-60-2)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / water / 5 h / Reflux

2: triethylamine / water; acetonitrile / 12 h / 20 °C

With hydrogenchloride; triethylamine; In water; acetonitrile;

DOI:10.1021/acs.orglett.1c04215

Reference yield:

iodomethylbenzene (620-05-3) → (R)-2-benzyl-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (706806-60-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C

1.2: 2 h / -78 - -30 °C

2.1: hydrogenchloride / water / 5 h / Reflux

3.1: triethylamine / water; acetonitrile / 12 h / 20 °C

With hydrogenchloride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; water; acetonitrile;

DOI:10.1021/acs.orglett.1c04215

upstream raw materials:

di-tert-butyl dicarbonate

(R)-2-benzylpyrrolidine-2-carboxylic acid

(2R,5R)-5-benzyl-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one

iodomethylbenzene

Downstream raw materials:

(R)-2-benzyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

C₂₃H₂₆BrN₃O₂

Refernces

• 1、 -. "Aryl pyrrolidinyl and piperidinyl ketone derivatives and uses thereof". Page/Page column 22. . Retrieved 2009/12/28.