Tert-butyl 5-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate

Base Information

• Chemical Name: Tert-butyl 5-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate
• CAS No.: 198835-06-2
• Molecular Formula: C11H17NO3
• Molecular Weight: 211
• Hs Code.: 2933990090
• European Community (EC) Number: 815-900-6
• DSSTox Substance ID: DTXSID20585546
• Mol file: 198835-06-2.mol

Synonyms:tert-butyl 5-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate;198835-06-2;2-BOC-5-OXO-2-AZA-BICYCLO[2.2.1]HEPTANE;2-AZABICYCLO[2.2.1]HEPTANE-2-CARBOXYLIC ACID, 5-OXO-, 1,1-DIMETHYLETHYL ESTER;MFCD09040745;tert-Butyl5-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate;MFCD22209795;MFCD30478162;5-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester;SCHEMBL1975869;DTXSID20585546;1932590-17-4;AKOS009132944;CS-W008809;PB29588;AM803459;BS-14027;SY042190;SY310808;SY318659;2-Boc-2-azabicyclo[2.2.1]heptan-5-one;EN300-37374;A814031;J-524841;(1R,4R)-2-Boc-2-azabicyclo[2.2.1]heptan-5-one;(1S,4S)-2-Boc-2-azabicyclo[2.2.1]heptan-5-one;Z255150056;tert-butyl5-oxo-2-aza-bicyclo[2.2.1]heptane-2-carboxylate;tert-Butyl 5-oxo-2-azabicyclo-[2.2.1]heptane-2-carboxylate;tert-butyl 5-oxidanylidene-2-azabicyclo[2.2.1]heptane-2-carboxylate

Chemical Property of Tert-butyl 5-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate

Chemical Property:

• Melting Point: 96 °C
• Boiling Point: 308 ?C
• PKA: -1.02±0.20(Predicted)
• Flash Point: 140 ?C
• PSA: 46.61000
• Density: 1.173
• LogP: 1.52270
• Storage Temp.: 2-8°C
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 211.12084340
• Heavy Atom Count: 15
• Complexity: 305

Purity/Quality:

97% ^*data from raw suppliers

tert-butyl5-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC2CC1CC2=O

Technology Process of Tert-butyl 5-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate

There total 14 articles about Tert-butyl 5-oxo-2-azabicyclo[2.2.1]heptane-2-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: 92.0%

rac-tert-butyl (1S,4S,5R)-5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate (198835-03-9,198835-07-3,1932042-59-5) → 5-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (198835-06-2)

Guidance literature:

With dipyridinium dichromate; In dichloromethane; at 20 ℃; for 96h; Molecular sieve;

DOI:10.1016/j.tet.2011.11.035

Reference yield: 71.0%

(1R,4R,5S)-tert-butyl 5-hydroxy-2-azabicyclo[2.2.1]heptanes-2-carboxylate (207405-69-4,198835-03-9,198835-07-3,1932042-59-5) → 5-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (1400808-00-5,198835-06-2)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; toluene; at 23 - 60 ℃; for 3h; Inert atmosphere;

Reference yield:

C11H19NO3 (1932042-59-5) → 5-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (198835-06-2)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 1h;

C₁₁H₁₉NO₃; With triethylamine; In dichloromethane; at -78 - 20 ℃; for 2h;

upstream raw materials:

oxalyl dichloride

(1R,4R)-1,1-Dimethylethyl 5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate

2-(tert-butoxycarbonyl)-2-azabicyclo[2.2.1]hept-5-ene

C₁₁H₁₉NO₃

Downstream raw materials:

5-oximino-2-azabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

endo-5-amino-2-azabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

exo-5-amino-2-azabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

tert-butyl (1RS,4RS,5RS)-5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate