tert-Butyl 2-methyl-4-oxopyrrolidine-1-carboxylate

Base Information

• Chemical Name: tert-Butyl 2-methyl-4-oxopyrrolidine-1-carboxylate
• CAS No.: 362706-25-0
• Molecular Formula: C10H17NO3
• Molecular Weight: 199.24700
• Hs Code.: 2933990090
• European Community (EC) Number: 836-981-4
• DSSTox Substance ID: DTXSID40593284
• Mol file: 362706-25-0.mol

Synonyms:tert-Butyl 2-methyl-4-oxopyrrolidine-1-carboxylate;362706-25-0;1-BOC-5-Methyl-3-pyrrolidinone;1-Boc-2-methyl-4-oxopyrrolidine;MFCD22376634;MFCD22665783;MFCD23381132;tert-Butyl2-methyl-4-oxopyrrolidine-1-carboxylate;SCHEMBL891999;N-Boc-5-methyl-3-pyrrolidinone;DTXSID40593284;ABBMDHUKQONVIE-UHFFFAOYSA-N;AMY27816;BCP21220;(R)-1-Boc-5-methyl-3-pyrrolidinone;(S)-1-Boc-5-methyl-3-pyrrolidinone;AKOS016011920;CS-W019809;DS-7042;PB39408;PB40461;PB42643;DA-18055;SY038568;SY038569;SY114669;F51791;EN300-1074120;A851525;2-Methyl-4-oxo-1-pyrrolidinecarboxylic acid tert-butyl ester

Chemical Property of tert-Butyl 2-methyl-4-oxopyrrolidine-1-carboxylate

Chemical Property:

• Boiling Point: 280 oC
• PKA: -1.72±0.40(Predicted)
• Flash Point: 123 oC
• PSA: 46.61000
• Density: 1.086
• LogP: 1.52270
• Storage Temp.: 2-8°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 199.12084340
• Heavy Atom Count: 14
• Complexity: 255

Purity/Quality:

97% ^*data from raw suppliers

tert-Butyl2-methyl-4-oxopyrrolidine-1-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(=O)CN1C(=O)OC(C)(C)C

Technology Process of tert-Butyl 2-methyl-4-oxopyrrolidine-1-carboxylate

There total 7 articles about tert-Butyl 2-methyl-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: 66.5%

(+,)-N-benzyl-5-methylpyrrolidin-3-one (23770-07-2) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 2-methyl-4-oxopyrrolidine-1-carboxylate (362706-25-0,1027775-28-5,1374673-93-4)

Guidance literature:

With hydrogen; palladium on carbon; In ethanol; under 2068.65 Torr;

Reference yield:

tert-butyl 4-hydroxy-2-methylpyrrolidine-1-carboxylate (156865-72-4,2299231-07-3) → tert-butyl 2-methyl-4-oxopyrrolidine-1-carboxylate (362706-25-0,1027775-28-5,1374673-93-4)

Guidance literature:

With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 20 ℃;

Reference yield:

1-[(1,1-dimethylethoxy)-carbonyl]-4-hydroxy-2-pyrrolidine carboxylic acid methyl ester (897046-42-3) → tert-butyl 2-methyl-4-oxopyrrolidine-1-carboxylate (362706-25-0,1027775-28-5,1374673-93-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 20 °C

2: lithium borohydride / tetrahydrofuran / 0 - 20 °C

3: triethylamine / dichloromethane / -10 - 20 °C

4: lithium triethylborohydride / tetrahydrofuran / 2 h / 20 °C

5: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C

6: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 20 °C

With 1H-imidazole; lithium borohydride; tetrabutyl ammonium fluoride; lithium triethylborohydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

(+,)-N-benzyl-5-methylpyrrolidin-3-one

di-tert-butyl dicarbonate

1-[(1,1-dimethylethoxy)-carbonyl]-4-hydroxy-2-pyrrolidine carboxylic acid methyl ester

tert-butyl 4-hydroxy-2-methylpyrrolidine-1-carboxylate

Downstream raw materials:

N-((R)-1-(3-chlorophenyl)ethyl)-5-methyl-2-((tetrahydro-2H-pyran-4-yl)amino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxamide