(3S,10bR)-10b-(3,4-Dimethoxy-benzyl)-8,9-dimethoxy-3-phenyl-2,3,6,10b-tetrahydro-oxazolo[2,3-a]isoquinolin-5-one

Base Information

• Chemical Name: (3S,10bR)-10b-(3,4-Dimethoxy-benzyl)-8,9-dimethoxy-3-phenyl-2,3,6,10b-tetrahydro-oxazolo[2,3-a]isoquinolin-5-one
• CAS No.: 178208-18-9
• Molecular Formula: C₂₈H₂₉NO₆
• Molecular Weight: 475.541
• Mol file: 178208-18-9.mol

Synonyms:(3S,10bR)-10b-(3,4-Dimethoxy-benzyl)-8,9-dimethoxy-3-phenyl-2,3,6,10b-tetrahydro-oxazolo[2,3-a]isoquinolin-5-one

Chemical Property of (3S,10bR)-10b-(3,4-Dimethoxy-benzyl)-8,9-dimethoxy-3-phenyl-2,3,6,10b-tetrahydro-oxazolo[2,3-a]isoquinolin-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,10bR)-10b-(3,4-Dimethoxy-benzyl)-8,9-dimethoxy-3-phenyl-2,3,6,10b-tetrahydro-oxazolo[2,3-a]isoquinolin-5-one

There total 1 articles about (3S,10bR)-10b-(3,4-Dimethoxy-benzyl)-8,9-dimethoxy-3-phenyl-2,3,6,10b-tetrahydro-oxazolo[2,3-a]isoquinolin-5-one 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: 90.0%

o-homoveratroylhomoveratric acid (26954-85-8) + (2S)-2-phenylglycinol (20989-17-7) → (3S,10bR)-10b-(3,4-Dimethoxy-benzyl)-8,9-dimethoxy-3-phenyl-2,3,6,10b-tetrahydro-oxazolo[2,3-a]isoquinolin-5-one (178208-18-9)

Guidance literature:

In toluene; for 14h; Heating;

DOI:10.1021/jo960110h

Reference yield: 90.0%

(3S,10bR)-10b-(3,4-Dimethoxy-benzyl)-8,9-dimethoxy-3-phenyl-2,3,6,10b-tetrahydro-oxazolo[2,3-a]isoquinolin-5-one (178208-18-9) → (S)-1-(3,4-Dimethoxy-benzyl)-2-((S)-2-hydroxy-1-phenyl-ethyl)-6,7-dimethoxy-1,4-dihydro-2H-isoquinolin-3-one (178208-19-0)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride; In toluene; at -30 ℃; for 6h;

DOI:10.1021/jo960110h

Reference yield:

(3S,10bR)-10b-(3,4-Dimethoxy-benzyl)-8,9-dimethoxy-3-phenyl-2,3,6,10b-tetrahydro-oxazolo[2,3-a]isoquinolin-5-one (178208-18-9) → S-(-)-Norlaudanosine (4747-98-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / Red-Al / toluene / 6 h / -30 °C

2: 84 percent / LiAlH₄ / tetrahydrofuran / 3 h

3: 82 percent / H₂, 1N HCl / Pd/C / ethanol / 12 h

With hydrogenchloride; lithium aluminium tetrahydride; hydrogen; sodium bis(2-methoxyethoxy)aluminium dihydride; palladium on activated charcoal; In tetrahydrofuran; ethanol; toluene;

DOI:10.1021/jo960110h

upstream raw materials:

o-homoveratroylhomoveratric acid

(2S)-2-phenylglycinol

Downstream raw materials:

(S)-1-(3,4-Dimethoxy-benzyl)-2-((S)-2-hydroxy-1-phenyl-ethyl)-6,7-dimethoxy-1,4-dihydro-2H-isoquinolin-3-one

(S)-1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-1,4-dihydro-2H-isoquinolin-3-one

C₂₀H₂₃NO₄

(S)-1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-3-oxo-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester