(+)-3,4,5,6,7,8-hexahydro-1-(p-Methoxybenzyl)-2(1H)-Isoquinolinecarboxaldehyde

Base Information

• Chemical Name: (+)-3,4,5,6,7,8-hexahydro-1-(p-Methoxybenzyl)-2(1H)-Isoquinolinecarboxaldehyde
• CAS No.: 51773-23-0
• Molecular Formula: C18H23NO2
• Molecular Weight: 285.386
• Mol file: 51773-23-0.mol

Synonyms:N-Formyl Octabase;

Chemical Property of (+)-3,4,5,6,7,8-hexahydro-1-(p-Methoxybenzyl)-2(1H)-Isoquinolinecarboxaldehyde

Chemical Property:

• Boiling Point: 466.8±38.0 °C(Predicted)
• PKA: -0.81±0.40(Predicted)
• PSA: 29.54000
• Density: 1.13±0.1 g/cm3(Predicted)
• LogP: 3.91280
• Storage Temp.: Room Temperature, under inert atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slig

Purity/Quality:

98.5% ^*data from raw suppliers

(R)-N-FormylOctabase ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (R)-N-Formyl Octabase is a by-product and R isomer in the synthesis of N-Formyl Octabase (F700890), which is used in the synthertic preparation of morphinans and isoquinoline alkaloids.

Technology Process of (+)-3,4,5,6,7,8-hexahydro-1-(p-Methoxybenzyl)-2(1H)-Isoquinolinecarboxaldehyde

There total 2 articles about (+)-3,4,5,6,7,8-hexahydro-1-(p-Methoxybenzyl)-2(1H)-Isoquinolinecarboxaldehyde 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:

(Z)-2-Formyl-1-<(4-methoxyphenyl)methylene>-1,2,3,4,5,6,7,8-octahydroisoquinoline (116172-20-4) → (S)-2-Formyl-1-<(4-methoxyphenyl)methyl>-1,2,3,4,5,6,7,8-octahydroispquinoline (29144-31-8) + (R)-2-Formyl-1-<(4-methoxyphenyl)methyl>-1,2,3,4,5,6,7,8-octahydroispquinoline (51773-23-0)

Guidance literature:

With ; hydrogen; In methanol; at 100 ℃; for 24h; under 45003.6 Torr; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/S0957-4166(00)82157-6

Reference yield:

1-(4-methoxybenzyl)-3,4,5,6,7,8-hexahydro-isoquinoline (51072-35-6) → (R)-2-Formyl-1-<(4-methoxyphenyl)methyl>-1,2,3,4,5,6,7,8-octahydroispquinoline (51773-23-0)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / tetrahydrofuran / 8 h / 0 °C

2: H₂ / Ru(CF₃COO)2<(R)-TolBINAP> / methanol / 164 h / 30 °C / 76000 Torr

With pyridine; hydrogen; Ru(CF3COO)2<(R)-TolBINAP>; In tetrahydrofuran; methanol;

DOI:10.1021/jo00081a007

upstream raw materials:

(Z)-2-Formyl-1-<(4-methoxyphenyl)methylene>-1,2,3,4,5,6,7,8-octahydroisoquinoline

1-(4-methoxybenzyl)-3,4,5,6,7,8-hexahydro-isoquinoline

Refernces

• 1、 Heiser,Broger,Crameri. "New efficient methods for the synthesis and in-situ preparation of ruthenium(II) complexes of atropisomeric diphosphines and their application in asymmetric catalytic hydrogenations". . p. 51 - 62. Retrieved 2007/12/18.