Tert-butyl 3-cyano-4-oxopyrrolidine-1-carboxylate

Base Information

• Chemical Name: Tert-butyl 3-cyano-4-oxopyrrolidine-1-carboxylate
• CAS No.: 175463-32-8
• Molecular Formula: C10H14N2O3
• Molecular Weight: 210.233
• Hs Code.: 29339900
• European Community (EC) Number: 700-004-9
• DSSTox Substance ID: DTXSID60373540
• Nikkaji Number: J1.647.136D
• Mol file: 175463-32-8.mol

Synonyms:175463-32-8;tert-butyl 3-cyano-4-oxopyrrolidine-1-carboxylate;1-Boc-3-cyano-4-oxopyrrolidine;1-Boc-3-cyano-4-pyrrolidinone;1-n-boc-3-cyanopyrrolidin-4-one;tert-Butyl 3-cyano-4-oxo-pyrrolidine-1-carboxylate;1-tert-Butoxycarbonyl-3-cyano-4-pyrrolidone;MFCD01318456;EC 700-004-9;1-PYRROLIDINECARBOXYLIC ACID, 3-CYANO-4-OXO-, 1,1-DIMETHYLETHYL ESTER;3-Cyano-4-oxopyrrolidine-1-carboxylic Acid tert-Butyl Ester;1-boc-3-cyano-4-pyrrolidone;N-Boc-3-Cyano-4-Pyrrolidinone;1-tert-Butoxycarbonyl-3-cyano-4-pyrrolidinone;SCHEMBL625040;1-n-boc-3-cyanopyrrolidone-4;DTXSID60373540;1-N-Boc-3-Cyanopyrrolid-4-One;RKUQLKRPWWYRIG-UHFFFAOYSA-N;1-n-boc-3-cyano-pyrrolidinone-4;1-N-Boc-3-Cyano-pyrrolid-4-one;AKOS005146242;CS-W002764;GS-4483;PB14230;SY003674;A3896;AM20090045;B4761;FT-0630202;EN300-91127;tert-butyl 3-cyano-4-oxopyrrolidine-1 carboxylate;Q-102172;1,1-dimethylethyl 3-cyano-4-oxo-1-pyrrolidinecarboxylate;2-Methyl-2-propanyl 3-cyano-4-oxo-1-pyrrolidinecarboxylate

Chemical Property of Tert-butyl 3-cyano-4-oxopyrrolidine-1-carboxylate

Chemical Property:

• Vapor Pressure: 2.17E-05mmHg at 25°C
• Melting Point: 160-167 °C
• Refractive Index: 1.499
• Boiling Point: 360.738 °C at 760 mmHg
• PKA: -4.24±0.40(Predicted)
• Flash Point: 171.968 °C
• PSA: 70.40000
• Density: 1.187 g/cm³
• LogP: 0.88388
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 210.10044231
• Heavy Atom Count: 15
• Complexity: 334

Purity/Quality:

99% ^*data from raw suppliers

1-Boc-3-cyano-4-pyrrolidinone ^*data from reagent suppliers

Safty Information:

• Statements: 20/21/22-36/37/38
• Safety Statements: 9-26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(C(=O)C1)C#N
• Uses: 1-Boc-3-cyano-4-pyrrolidinone is used in the synthesis of new napthyridone antibacterials. Also used in the synthesis of gemifloxacin derivatives containing benzyloxime moiety.

Technology Process of Tert-butyl 3-cyano-4-oxopyrrolidine-1-carboxylate

There total 7 articles about Tert-butyl 3-cyano-4-oxopyrrolidine-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: 83.0%

[tert-butoxycarbonyl-(2-cyanoethyl)amino]acetic acid methyl ester (266353-19-9) → 3-cyano-4-oxopyrrolidine-1-carboxylic acid tert-butyl ester (175463-32-8)

Guidance literature:

[tert-butoxycarbonyl-(2-cyanoethyl)amino]acetic acid methyl ester; With sodium methylate; In toluene; at 80 ℃; for 3h;

With hydrogenchloride; at 22 ℃; for 2h;

DOI:10.1021/jm049076m

Reference yield: 75.0%

N-tert-butoxycarbonyl-2-(2-cyanoethyl)aminoacetic acid ethyl ester (266353-18-8) → 3-cyano-4-oxopyrrolidine-1-carboxylic acid tert-butyl ester (175463-32-8)

Guidance literature:

With sodium hydride; In toluene; for 1.5h; Reflux;

DOI:10.1002/ardp.201000160

Reference yield:

N-cyanoethyl glycine ethyl ester (44981-94-4) → 3-cyano-4-oxopyrrolidine-1-carboxylic acid tert-butyl ester (175463-32-8)

Guidance literature:

Multi-step reaction with 2 steps

1: CH₂Cl₂ / 1 h / 20 °C

2: NaOEt / ethanol / 3 h / Heating

With sodium ethanolate; In ethanol; dichloromethane; 2: Dieckmann reaction;

DOI:10.1016/j.bmcl.2003.09.039

upstream raw materials:

N-tert-butoxycarbonyl-2-(2-cyanoethyl)aminoacetic acid ethyl ester

N-cyanoethyl glycine ethyl ester

di-tert-butyl dicarbonate

[tert-butoxycarbonyl-(2-cyanoethyl)amino]acetic acid methyl ester

Downstream raw materials:

3-amino-4,6-dihydro-1H-pyrrolo[3,4-c]pyrazole-5-carboxylic acid tert-butyl ester

tert-butyl 3-(aminomethyl)-4-hydroxypyrrolidine-1-carboxylate

3-amino-2,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-5-carboxylic acid tert-butyl ester

4-cyano-3-amino-1-(N-tert-butoxycarbonyl)-3,4-pyrroline