Cyclobutyl-[(R)-1-(4-methoxy-benzyl)-3,4,5,6,7,8-hexahydro-1H-isoquinolin-2-yl]-methanone

Base Information

• Chemical Name: Cyclobutyl-[(R)-1-(4-methoxy-benzyl)-3,4,5,6,7,8-hexahydro-1H-isoquinolin-2-yl]-methanone
• CAS No.: 66209-45-8
• Molecular Formula: C₂₂H₂₉NO₂
• Molecular Weight: 339.478
• Mol file: 66209-45-8.mol

Synonyms:

Chemical Property of Cyclobutyl-[(R)-1-(4-methoxy-benzyl)-3,4,5,6,7,8-hexahydro-1H-isoquinolin-2-yl]-methanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Cyclobutyl-[(R)-1-(4-methoxy-benzyl)-3,4,5,6,7,8-hexahydro-1H-isoquinolin-2-yl]-methanone

There total 6 articles about Cyclobutyl-[(R)-1-(4-methoxy-benzyl)-3,4,5,6,7,8-hexahydro-1H-isoquinolin-2-yl]-methanone 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:

Cyclobutanecarboxylic acid (3721-95-7) + (+/-)-1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline hydrobromide (93477-35-1) → 2-cyclobutylcarbonyl-1-(p-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline (66209-45-8,69761-88-2,94230-89-4)

Guidance literature:

With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; ethyl acetate; Large scale;

Reference yield:

1-(4-Methoxy-benzyl)-2-methyl-3,4,5,6,7,8-hexahydro-1H-isoquinoline 2-oxide → 2-cyclobutylcarbonyl-1-(p-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline (66209-45-8,69761-88-2,94230-89-4)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. FeCl₂ / CH₂Cl₂ / 1.) -14 to -10 deg C, 1 h; 2.) room temp., 2 h

2: triethylamine

With triethylamine; iron(II) chloride; In dichloromethane;

DOI:10.1055/s-1985-31342

Reference yield:

1-(p-methoxybenzyl)-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline (38969-65-2,31414-58-1) → 2-cyclobutylcarbonyl-1-(p-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline (66209-45-8,69761-88-2,94230-89-4)

Guidance literature:

Multi-step reaction with 3 steps

1: m-chloroperbenzoic acid / CH₂Cl₂ / 0.33 h / -14 - -10 °C

2: aq. FeCl₂ / CH₂Cl₂ / 1.) -14 to -10 deg C, 1 h; 2.) room temp., 2 h

3: triethylamine

With triethylamine; 3-chloro-benzenecarboperoxoic acid; iron(II) chloride; In dichloromethane;

DOI:10.1055/s-1985-31342

upstream raw materials:

(+)-1-(p-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline

Cyclobutanecarbonyl chloride

1-(p-methoxybenzyl)-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline

Cyclobutanecarboxylic acid

Refernces

• 1、 Monkovic, Ivo,Wong, Henry,Bachand, Carol. "Secondary Amines from the Iron(II) Ion-Catalyzed Reaction of Amine Oxides: A General Method for the Dealkylation of Tertiary Amines". . p. 770 - 773. Retrieved 2007/10/02.
• 2、 -. "Process of N-demethylating (-)-1-(p-methoxybenzyl)-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline". . . Retrieved 2008/06/13.