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

Base Information

Chemical Name:exo/endo-benzyl 7-(hydroxymethyl)-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylate
CAS No.:1253521-29-7
Molecular Formula:C₁₆H₁₇NO₃
Molecular Weight:271.316
Hs Code.:

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

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

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

There total 1 articles about exo/endo-benzyl 7-(hydroxymethyl)-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:

: 79328-85-1
N-benzyloxycarbonyl-1,2-dihydropyridine

: 107-02-8,25068-14-8
acrolein

: 1253521-29-7
exo/endo-benzyl 7-(hydroxymethyl)-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylate

Guidance literature:: N-benzyloxycarbonyl-1,2-dihydropyridine; acrolein; With trifluoroacetic acid; In water; acetonitrile; at 0 ℃; for 24h;

With sodium methylate; In methanol; at 20 ℃; for 12h;

Reference yield:

: 1253521-29-7
exo/endo-benzyl 7-(hydroxymethyl)-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylate

: benzyl (1S,4S,7S)-7-(hydroxymethyl)-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylate

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

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

: C₁₆H₁₉NO₃

Guidance literature:: With sodium tetrahydroborate; In ethanol; at 20 ℃; for 1h; optical yield given as %ee;
DOI:10.1039/c0cc00110d

Reference yield:

: 1253521-29-7
exo/endo-benzyl 7-(hydroxymethyl)-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

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium tetrahydroborate / ethanol / 0 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.33 h / -78 °C / Inert atmosphere

2.2: 0.33 h / -78 °C / Inert atmosphere

With sodium tetrahydroborate; oxalyl dichloride; dimethyl sulfoxide; In ethanol; dichloromethane;
DOI:10.1021/jo200745n