(4aS,8aS)-2-[(1R)-2-hydroxy-1-phenylethyl]-perhydroisoquinoline

Base Information

• Chemical Name: (4aS,8aS)-2-[(1R)-2-hydroxy-1-phenylethyl]-perhydroisoquinoline
• CAS No.: 864967-40-8
• Molecular Formula: C₁₇H₂₅NO
• Molecular Weight: 259.392
• Mol file: 864967-40-8.mol

Synonyms:(4aS,8aS)-2-[(1R)-2-hydroxy-1-phenylethyl]-perhydroisoquinoline

Chemical Property of (4aS,8aS)-2-[(1R)-2-hydroxy-1-phenylethyl]-perhydroisoquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aS,8aS)-2-[(1R)-2-hydroxy-1-phenylethyl]-perhydroisoquinoline

There total 4 articles about (4aS,8aS)-2-[(1R)-2-hydroxy-1-phenylethyl]-perhydroisoquinoline 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: 65.0%

(3R,6aS,10aS,10bR)-5-oxo-3-phenyl-perhydrooxazolo[2,3-a]isoquinoline (864967-38-4) → (4aS,8aS)-2-[(1R)-2-hydroxy-1-phenylethyl]-perhydroisoquinoline (864967-40-8)

Guidance literature:

With lithium aluminium tetrahydride; aluminium trichloride; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/ol051242c

Reference yield:

(3R,6aR,10aS,10bR)-6-benzyloxycarbonyl-5-oxo-3-phenyl-2,3,6,6a,7,10,10a,10b-octahydro-5H-oxazolo[2,3-a]isoquinoline (864967-36-2) → (4aS,8aS)-2-[(1R)-2-hydroxy-1-phenylethyl]-perhydroisoquinoline (864967-40-8)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / Pd-C / methanol / 48 h / 25 °C

2: 287 mg / toluene / 12 h / Heating

3: 65 percent / LiAlH₄; AlCl₃ / tetrahydrofuran / -78 - 20 °C

With lithium aluminium tetrahydride; aluminium trichloride; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; toluene;

DOI:10.1016/j.tet.2007.01.072

Reference yield:

(3R,7R,8S,8aR)-7,8-diallyl-6-benzyloxycarbonyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine → (4aS,8aS)-2-[(1R)-2-hydroxy-1-phenylethyl]-perhydroisoquinoline (864967-40-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / (1,3-dimesityl-4-imidazolin-2-yl)(PhCH=)RuCl₂(PCy₃) / CH₂Cl₂ / 2 h / 20 °C

2: H₂ / Pd/C

3: toluene / Heating

4: 65 percent / LiAlH₄; AlCl₃ / tetrahydrofuran / 20 °C

With lithium aluminium tetrahydride; aluminium trichloride; hydrogen; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/ol051242c

upstream raw materials:

(3R,6aS,10aS,10bR)-5-oxo-3-phenyl-perhydrooxazolo[2,3-a]isoquinoline

(3R,6aR,10aS,10bR)-6-benzyloxycarbonyl-5-oxo-3-phenyl-2,3,6,6a,7,10,10a,10b-octahydro-5H-oxazolo[2,3-a]isoquinoline