(1R,5S)-8-(tert-butyloxycarbonyl)-8-azabicyclo[3.2.1]-2-octanone

Base Information

• Chemical Name: (1R,5S)-8-(tert-butyloxycarbonyl)-8-azabicyclo[3.2.1]-2-octanone
• CAS No.: 208037-77-8
• Molecular Formula: C₁₂H₁₉NO₃
• Molecular Weight: 225.288
• Mol file: 208037-77-8.mol

Synonyms:(1R,5S)-8-(tert-butyloxycarbonyl)-8-azabicyclo[3.2.1]-2-octanone

Chemical Property of (1R,5S)-8-(tert-butyloxycarbonyl)-8-azabicyclo[3.2.1]-2-octanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,5S)-8-(tert-butyloxycarbonyl)-8-azabicyclo[3.2.1]-2-octanone

There total 8 articles about (1R,5S)-8-(tert-butyloxycarbonyl)-8-azabicyclo[3.2.1]-2-octanone 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: 96.0%

di-tert-butyl dicarbonate (24424-99-5) + (1R,5S)-8-benzyl-8-azabicyclo[3.2.1]octan-2-one (208037-76-7) → (1R,5S)-8-(tert-butyloxycarbonyl)-8-azabicyclo[3.2.1]-2-octanone (208037-77-8,1408076-39-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 5h;

DOI:10.1021/jo980153t

Reference yield: 87.0%

(1R,5S)-2-Hydroxy-8-aza-bicyclo[3.2.1]oct-2-ene-3,8-dicarboxylic acid 8-tert-butyl ester 3-methyl ester (208037-90-5) → (1R,5S)-8-(tert-butyloxycarbonyl)-8-azabicyclo[3.2.1]-2-octanone (208037-77-8,1408076-39-0)

Guidance literature:

With sodium iodide; In pyridine; for 7.5h;

DOI:10.1021/jo980153t

Reference yield:

(2R,5S)-5-[1'-(2'-methoxycarbonyl)ethyl]proline methyl ester (208037-73-4) → (1R,5S)-8-(tert-butyloxycarbonyl)-8-azabicyclo[3.2.1]-2-octanone (208037-77-8,1408076-39-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / Et₃N / methanol / 14 h / Ambient temperature

2: 85 percent / KHMDS / tetrahydrofuran / 6 h / -78 °C

3: 87 percent / NaI / pyridine / 7.5 h

With potassium hexamethylsilazane; triethylamine; sodium iodide; In tetrahydrofuran; pyridine; methanol;

DOI:10.1021/jo980153t

upstream raw materials:

di-tert-butyl dicarbonate

(1R,5S)-8-benzyl-8-azabicyclo[3.2.1]octan-2-one

(1R,5S)-2-Hydroxy-8-aza-bicyclo[3.2.1]oct-2-ene-3,8-dicarboxylic acid 8-tert-butyl ester 3-methyl ester

(2R,5S)-5-[1'-(2'-methoxycarbonyl)ethyl]proline methyl ester

Downstream raw materials:

RTI-128

Benzoic acid (1R,2R,3S,5S)-2-carbamoyl-8-aza-bicyclo[3.2.1]oct-3-yl ester

(1R,2R,3S,5S)-3-Benzoyloxy-2-carbamoyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

benzylecgonine