benzyl 7-formyl-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylate

Base Information

• Chemical Name: benzyl 7-formyl-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylate
• CAS No.: 1151764-22-5
• Molecular Formula: C₁₆H₁₇NO₃
• Molecular Weight: 271.316
• Mol file: 1151764-22-5.mol

Synonyms:benzyl 7-formyl-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylate

Chemical Property of benzyl 7-formyl-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of benzyl 7-formyl-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylate

There total 10 articles about benzyl 7-formyl-2-azabicyclo[2.2.2]oct-5-ene-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: 90.0%

N-benzyloxycarbonyl-1,2-dihydropyridine (79328-85-1) + acrolein (107-02-8,25068-14-8) → benzyl 7-formyl-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylate (1151764-22-5)

Guidance literature:

With (2S,4S)-4-tert-butyl-2,5,5-triphenyl-oxazolidine trifluoroacetate; In water; acetonitrile; at 0 ℃; for 24h; optical yield given as %ee; enantioselective reaction;

DOI:10.1039/c0cc00110d

Reference yield:

N-benzyloxycarbonyl-1,2-dihydropyridine (79328-85-1) + acrolein (107-02-8,25068-14-8) → benzyl (5-formylcyclohexa-2,4-dien-1-yl)methylcarbamate + benzyl 7-formyl-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylate (1151764-22-5)

Guidance literature:

With (R)-5-benzyl-2,2,3-trimethyl-4-imidazolidinone hydrochloride; In water; acetonitrile; at 20 ℃; for 14h; Title compound not separated from byproducts.;

DOI:10.1002/anie.200701754

Reference yield:

N-benzyloxycarbonyl-1,2-dihydropyridine (79328-85-1) + acrolein (107-02-8,25068-14-8) → benzyl 7-formyl-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylate (1151764-22-5) + benzyl 7-formyl-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylate (1190307-41-5) + C16H17NO3 + C16H17NO3

Guidance literature:

With (2S,4S)-4-tert-butyl-2,5,5-triphenyl-oxazolidine trifluoroacetate; In water; acetonitrile; at 0 ℃; for 24h; optical yield given as %ee; enantioselective reaction;

DOI:10.1039/c0cc00110d

upstream raw materials:

N-benzyloxycarbonyl-1,2-dihydropyridine

acrolein

pyridine

exo/endo-benzyl 7-(hydroxymethyl)-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylate