tert-butyl 5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate

Base Information

• Chemical Name: tert-butyl 5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate
• CAS No.: 207405-60-5
• Molecular Formula: C11H19NO3
• Molecular Weight: 213.277
• Hs Code.: 2933990090
• European Community (EC) Number: 800-233-5
• DSSTox Substance ID: DTXSID10596323
• Mol file: 207405-60-5.mol

Synonyms:[exo] 2-aza-2-(t-butoxycarbonyl)-bicyclo[2.2.1]heptan-5-ol;2-aza-2-(t-butoxycarbonyl)-bicyclo[2.2.1]heptan-5-ol;(1R,4R,5S)-tert-butyl 5-hydroxy-2-azabicyclo[2.2.1]heptanes-2-carboxylate;tert-butyl 5-hydroxy-2-aza-bicyclo[2.2.1]heptane-2-carboxylate;(1R,4R)-1,1-Dimethylethyl 5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate;WT1526;5-hydroxy-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester;tertbutyl-5-hydroxy-2-aza-bicyclo[2.2.1]heptanes-2-carboxylate;

Chemical Property of tert-butyl 5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate

Chemical Property:

• Boiling Point: 310.3±35.0 °C(Predicted)
• PKA: 14.70±0.20(Predicted)
• PSA: 49.77000
• Density: 1.181±0.06 g/cm3(Predicted)
• LogP: 1.31450
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 213.13649347
• Heavy Atom Count: 15
• Complexity: 272

Purity/Quality:

99% ^*data from raw suppliers

tert-Butyl 5-hydroxy-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)N1CC2CC1CC2O

Technology Process of tert-butyl 5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate

There total 1 articles about tert-butyl 5-hydroxy-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:

2-(tert-butoxycarbonyl)-2-azabicyclo[2.2.1]hept-5-ene (188345-71-3) → tert-butyl 6-hydroxy-2-azabicyclo[2,2,1]heptane-2-carboxylate (1099570-25-8,198835-02-8,198835-05-1,207405-59-2) + (1R,4R)-1,1-Dimethylethyl 5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate (207405-60-5,198835-03-9,198835-07-3,1932042-59-5)

Guidance literature:

With sodium hydroxide; borane; dihydrogen peroxide; potassium carbonate; In tetrahydrofuran; water; ethyl acetate;

Reference yield: 86.0%

(1R,4R)-1,1-Dimethylethyl 5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate (207405-60-5,198835-03-9,198835-07-3,1932042-59-5) + 3-fluoro-5-(5-methyl-1,3-thiazol-2-yl)benzonitrile → tert-butyl 5-[3-cyano-5-(5-methylthiazol-2-yl)phenoxy]-2-azabicyclo[2.2.1]heptane-2-carboxylate

Guidance literature:

(1R,4R)-1,1-Dimethylethyl 5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; for 1.5h;

3-fluoro-5-(5-methyl-1,3-thiazol-2-yl)benzonitrile; In N,N-dimethyl-formamide; mineral oil; at 20 ℃;

Reference yield:

2-(2-bromoethoxy)tetrahydropyran (17739-45-6,59146-56-4) + (1R,4R)-1,1-Dimethylethyl 5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate (207405-60-5,198835-03-9,198835-07-3,1932042-59-5) → tert-butyl 5-(2-tetrahydropyran-2-yloxyethoxy)-2-azabicyclo[2.2.1]heptane-2-carboxylate (1437774-64-5)

Guidance literature:

With tetrabutylammomium bromide; sodium hydroxide; In toluene; at 60 ℃;

upstream raw materials:

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

Downstream raw materials:

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

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

benzyl 5-({cis-4-[2-(benzyloxy)-2-oxoethyl]cyclohexyl}oxy)-2-azabicyclo[2.2.1]heptane-2-carboxylate

tert-butyl 5-(2-tetrahydropyran-2-yloxyethoxy)-2-azabicyclo[2.2.1]heptane-2-carboxylate

Refernces