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

Base Information

• Chemical Name: (2S,4R)-1-(tert-butoxycarbonyl)-4-cyanopyrrolidine-2-carboxylic acid
• CAS No.: 273221-94-6
• Molecular Formula: C11H16 N2 O4
• Molecular Weight: 240.25600
• Hs Code.: 2933998090
• European Community (EC) Number: 688-951-3
• DSSTox Substance ID: DTXSID20590519
• Wikidata: Q72510101
• Mol file: 273221-94-6.mol

Synonyms:273221-94-6;(2S,4R)-1-(tert-butoxycarbonyl)-4-cyanopyrrolidine-2-carboxylic acid;N-Boc-trans-4-cyano-L-proline;(2S,4R)-4-cyano-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid;4-Cyano-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester;trans-N-Boc-4-cyano-L-proline;(S)-Boc-trans-4-cyanoproline;SCHEMBL1269658;(2S,4R)-1-[(tert-butoxy)carbonyl]-4-cyanopyrrolidine-2-carboxylic acid;DTXSID20590519;MIVXQYMYEMUMKK-YUMQZZPRSA-N;(4R)-1-Boc-4-cyano-L-proline;MFCD01860670;AKOS015969285;AS-47738;DB-067766;CS-0254826;A26549;F15964;(4R)-1-(tert-Butoxycarbonyl)-4-cyano-L-proline;J-016735

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

Chemical Property:

• Boiling Point: 423.5±45.0 °C(Predicted)
• PKA: 3.51±0.40(Predicted)
• PSA: 90.63000
• Density: 1.25
• LogP: 1.15808
• Storage Temp.: 2-8°C
• Water Solubility.: Slightly soluble in water.
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 240.11100700
• Heavy Atom Count: 17
• Complexity: 377

Purity/Quality:

99% ^*data from raw suppliers

N-Boc-trans-4-cyano-L-proline ^*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)C#N
• Isomeric SMILES: CC(C)(C)OC(=O)N1C[C@@H](C[C@H]1C(=O)O)C#N
• Uses: trans-N-Boc-4-cyano-L-proline is used as pharmaceutical intermediate.

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

There total 5 articles about (2S,4R)-1-(tert-butoxycarbonyl)-4-cyanopyrrolidine-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:

1-(tert-butyl) 2-methyl (2S,4R)-4-cyanopyrrolidine-1 ,2-dicarboxylate (194163-91-2) → (2S,4R)-4-cyano-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (273221-94-6)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 0 ℃; for 16h; Inert atmosphere;

DOI:10.1002/chem.202101373

Reference yield:

2’-methyl-2’-propanyl (1S,4S)-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate (87250-97-3,113775-22-7) → (2S,4R)-4-cyano-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (273221-94-6)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium azide / methanol / 16 h / 40 °C / Inert atmosphere

2: triethylamine / dichloromethane / 16 h / 0 °C / Inert atmosphere

3: dimethyl sulfoxide / 4 h / 80 °C / Inert atmosphere

4: lithium hydroxide / tetrahydrofuran; water / 16 h / 0 °C / Inert atmosphere

With sodium azide; triethylamine; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1002/chem.202101373

Reference yield:

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid (13726-69-7,946610-68-0) → (2S,4R)-4-cyano-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (273221-94-6)

Guidance literature:

Multi-step reaction with 5 steps

1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 20 h / 0 - 20 °C / Inert atmosphere

2: sodium azide / methanol / 16 h / 40 °C / Inert atmosphere

3: triethylamine / dichloromethane / 16 h / 0 °C / Inert atmosphere

4: dimethyl sulfoxide / 4 h / 80 °C / Inert atmosphere

5: lithium hydroxide / tetrahydrofuran; water / 16 h / 0 °C / Inert atmosphere

With sodium azide; di-isopropyl azodicarboxylate; triethylamine; triphenylphosphine; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1002/chem.202101373

upstream raw materials:

2’-methyl-2’-propanyl (1S,4S)-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester

(2S,4S)-2-methyl N-Boc-4-((methylsulfonyl)oxy)pyrrolidine-2-carboxylate

Downstream raw materials:

{(2S,5S)-2-[5-(4'-{2-[(2S,4R)-4-Cyano-1-((S)-2-methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester

((S)-1-{(2S,4R)-2-[5-(4-Bromo-phenyl)-1H-imidazol-2-yl]-4-cyano-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester

(3R,5S)-5-(5-(4-bromophenyl)-1H-imidazol-2-yl)pyrrolidine-3-carbonitrile hydrochloride

(2S,4R)-2-[5-(4-Bromo-phenyl)-1H-imidazol-2-yl]-4-cyano-pyrrolidine-1-carboxylic acid tert-butyl ester

Refernces