(1R,5S)-N-benzyloxycarbonyl-2-oxo-8-azabicyclo[3.2.1]octane

Base Information

• Chemical Name: (1R,5S)-N-benzyloxycarbonyl-2-oxo-8-azabicyclo[3.2.1]octane
• CAS No.: 936564-33-9
• Molecular Formula: C₁₅H₁₇NO₃
• Molecular Weight: 259.305
• Mol file: 936564-33-9.mol

Synonyms:(1R,5S)-N-benzyloxycarbonyl-2-oxo-8-azabicyclo[3.2.1]octane

Chemical Property of (1R,5S)-N-benzyloxycarbonyl-2-oxo-8-azabicyclo[3.2.1]octane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,5S)-N-benzyloxycarbonyl-2-oxo-8-azabicyclo[3.2.1]octane

There total 2 articles about (1R,5S)-N-benzyloxycarbonyl-2-oxo-8-azabicyclo[3.2.1]octane 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: 56.0%

(5S)-8-methyl-8-azabicyclo[3.2.1]octan-2-one (56620-28-1) + benzyl chloroformate (501-53-1,94274-21-2) → (1R,5S)-N-benzyloxycarbonyl-2-oxo-8-azabicyclo[3.2.1]octane (936564-33-9)

Guidance literature:

With potassium carbonate; In toluene; for 48h; Heating;

DOI:10.1021/jo062532p

Reference yield:

C8H10N4O + benzyl chloroformate (501-53-1,94274-21-2) → (1R,5S)-N-benzyloxycarbonyl-2-oxo-8-azabicyclo[3.2.1]octane (936564-33-9)

Guidance literature:

C₈H₁₀N₄O; With hydrogenchloride; In water; at 0 ℃; Reflux;

With sodium carbonate; In water; pH=9.5 - 10;

benzyl chloroformate; With sodium carbonate; In methanol; water; at 0 - 20 ℃;

DOI:10.1016/j.tet.2010.04.037

Reference yield: 95.0%

(1R,5S)-N-benzyloxycarbonyl-2-oxo-8-azabicyclo[3.2.1]octane (936564-33-9) + trimethyl orthoformate (149-73-5) → (1R,5S)-N-benzyloxycarbonyl-2-methoxy-8-azabicyclo[3.2.1]oct-2-ene (936564-35-1)

Guidance literature:

With toluene-4-sulfonic acid; at 80 ℃; for 5h;

DOI:10.1021/jo062532p

upstream raw materials:

(5S)-8-methyl-8-azabicyclo[3.2.1]octan-2-one

benzyl chloroformate

Downstream raw materials:

(1R,5S)-N-benzyloxycarbonyl-2-methoxy-8-azabicyclo[3.2.1]oct-2-ene

(2R,5S)-N-benzyloxycarbonyl-2-methoxycarbonyl-5-(2-oxoethyl)-pyrrolidine

(2R,5S)-N-benzyloxycarbonyl-2-methoxycarbonyl-5-(2,2-dimethoxyethyl)-pyrrolidine

(1S,3aS)-1-(2-(tert-butyldiphenylsilyloxy)ethyl)-1,2,3,3a,4,5,8,9-octahydropyrrolo-[1,2-a]quinolin-6(7H)-one