(1R,4R,7R)-7-hydroxymethyl-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylic acid phenyl ester

Base Information

• Chemical Name: (1R,4R,7R)-7-hydroxymethyl-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylic acid phenyl ester
• CAS No.: 1239475-29-6
• Molecular Formula: C₁₅H₁₇NO₃
• Molecular Weight: 259.305

Synonyms:(1R,4R,7R)-7-hydroxymethyl-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylic acid phenyl ester

Chemical Property of (1R,4R,7R)-7-hydroxymethyl-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylic acid phenyl ester

Chemical Property:

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Technology Process of (1R,4R,7R)-7-hydroxymethyl-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylic acid phenyl ester

There total 4 articles about (1R,4R,7R)-7-hydroxymethyl-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylic acid phenyl ester 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:

1-(phenoxycarbonyl)-1,2-dihydropyridine (79328-86-2) + acrolein (107-02-8,25068-14-8) → (1R,4R,7R)-7-hydroxymethyl-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylic acid phenyl ester (1239475-29-6) + (1R,4R,7S)-7-hydroxymethyl-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylic acid phenyl ester + (1S,4S,7R)-7-hydroxymethyl-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylic acid phenyl ester (1333309-66-2) + (1S,4S,7S)-7-hydroxymethyl-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylic acid phenyl ester (1239475-08-1)

Guidance literature:

1-(phenoxycarbonyl)-1,2-dihydropyridine; acrolein; With (S)-2-hydroxy-1,2,2-triphenylethanaminium trifluoroacetate; In water; acetonitrile; at -25 - 0 ℃;

With sodium tetrahydroborate; In ethanol; at 0 - 20 ℃; optical yield given as %ee; stereoselective reaction;

DOI:10.1016/j.tetlet.2011.06.109

Reference yield:

C16H17NO4 (916605-48-6) → (1R,4R,7R)-7-hydroxymethyl-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylic acid phenyl ester (1239475-29-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1039/c0cc00110d

Reference yield:

C15H15NO3 → (1R,4R,7R)-7-hydroxymethyl-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylic acid phenyl ester (1239475-29-6) + (1S,4S,7S)-7-hydroxymethyl-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylic acid phenyl ester (1239475-08-1)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 20 ℃; for 1h; optical yield given as %ee;

DOI:10.1039/c0cc00110d

upstream raw materials:

C₁₆H₁₇NO₄

1-(phenoxycarbonyl)-1,2-dihydropyridine

acrolein

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