dimethyl 2-[(1-methoxymethyl-2-methyl-propylimino)-phenyl-methyl]-3-methyl-2-azabicyclo[2.2.2]oct-7-ene-5,6-dicarboxylate

Base Information

• Chemical Name: dimethyl 2-[(1-methoxymethyl-2-methyl-propylimino)-phenyl-methyl]-3-methyl-2-azabicyclo[2.2.2]oct-7-ene-5,6-dicarboxylate
• CAS No.: 873545-83-6
• Molecular Formula: C₂₅H₃₄N₂O₅
• Molecular Weight: 442.555

Synonyms:dimethyl 2-[(1-methoxymethyl-2-methyl-propylimino)-phenyl-methyl]-3-methyl-2-azabicyclo[2.2.2]oct-7-ene-5,6-dicarboxylate

Chemical Property of dimethyl 2-[(1-methoxymethyl-2-methyl-propylimino)-phenyl-methyl]-3-methyl-2-azabicyclo[2.2.2]oct-7-ene-5,6-dicarboxylate

Chemical Property:

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Technology Process of dimethyl 2-[(1-methoxymethyl-2-methyl-propylimino)-phenyl-methyl]-3-methyl-2-azabicyclo[2.2.2]oct-7-ene-5,6-dicarboxylate

There total 2 articles about dimethyl 2-[(1-methoxymethyl-2-methyl-propylimino)-phenyl-methyl]-3-methyl-2-azabicyclo[2.2.2]oct-7-ene-5,6-dicarboxylate 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:

(1R,2S,6S,7S,9R)-8-{[(E)-(S)-1-Methoxymethyl-2-methyl-propylimino]-phenyl-methyl}-9-methyl-4-oxa-8-aza-tricyclo[5.2.2.02,6]undec-10-ene-3,5-dione + methanol (67-56-1) → dimethyl 2-[(1-methoxymethyl-2-methyl-propylimino)-phenyl-methyl]-3-methyl-2-azabicyclo[2.2.2]oct-7-ene-5,6-dicarboxylate (873545-83-6)

Guidance literature:

With thionyl chloride; In dichloromethane; at 20 ℃; for 48h;

DOI:10.1021/ol052436v

Reference yield:

N-[(1S)-1-(methoxymethyl)-2-methylpropyl]-N-[(1E)-[(2R)-2-methylpyridin-1(2H)-yl](phenyl)methylene]amine (386253-22-1) → dimethyl 2-[(1-methoxymethyl-2-methyl-propylimino)-phenyl-methyl]-3-methyl-2-azabicyclo[2.2.2]oct-7-ene-5,6-dicarboxylate (873545-83-6)

Guidance literature:

Multi-step reaction with 2 steps

1: CH₂Cl₂ / 18 h / 20 °C

2: thionyl chloride / CH₂Cl₂ / 48 h / 20 °C

With thionyl chloride; In dichloromethane;

DOI:10.1021/ol052436v

Reference yield:

dimethyl 2-[(1-methoxymethyl-2-methyl-propylimino)-phenyl-methyl]-3-methyl-2-azabicyclo[2.2.2]oct-7-ene-5,6-dicarboxylate (873545-83-6) → {5-hydroxymethyl-2-[(1-methoxymethyl-2-methyl-propylimino)-phenyl-methyl]-3-methyl-2-aza-bicyclo[2.2.2]oct-7-en-6-yl}-methanol (873545-85-8)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; dichloromethane; at 20 ℃; for 2.5h;

DOI:10.1021/ol052436v

upstream raw materials:

methanol

N-[(1S)-1-(methoxymethyl)-2-methylpropyl]-N-[(1E)-[(2R)-2-methylpyridin-1(2H)-yl](phenyl)methylene]amine

Downstream raw materials:

{5-hydroxymethyl-2-[(1-methoxymethyl-2-methyl-propylimino)-phenyl-methyl]-3-methyl-2-aza-bicyclo[2.2.2]oct-7-en-6-yl}-methanol

(7,8-bis-benzyloxymethyl-3-methyl-2-aza-bicyclo[2.2.2]oct-5-en-2-yl)-phenyl-methanone

[(7,8-bis-benzyloxymethyl-3-methyl-2-aza-bicyclo[2.2.2]oct-5-en-2-yl)-phenyl-methylene]-(1-methoxymethyl-2-methyl-propyl)-amine

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