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

Base Information

Chemical Name:(3R,6aR,10aS,10bR)-6-(methoxycarbonyl)-5-oxo-3-phenyl-2,3,6,6a,7,10,10a,10b-octahydro-5H-oxazolo[2,3-a]isoquinoline
CAS No.:864967-37-3
Molecular Formula:C₁₉H₂₁NO₄
Molecular Weight:327.38
Hs Code.:

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

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

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

There total 5 articles about (3R,6aR,10aS,10bR)-6-(methoxycarbonyl)-5-oxo-3-phenyl-2,3,6,6a,7,10,10a,10b-octahydro-5H-oxazolo[2,3-a]isoquinoline 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: 85.0%

: 864967-35-1
(3R,7R,8S,8aR)-7,8-diallyl-6-(methoxycarbonyl)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

: 864967-37-3
(3R,6aR,10aS,10bR)-6-(methoxycarbonyl)-5-oxo-3-phenyl-2,3,6,6a,7,10,10a,10b-octahydro-5H-oxazolo[2,3-a]isoquinoline

Guidance literature:: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/ol051242c

Reference yield:

: 864967-32-8
(3R,8R,8aR)-8-allyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

: 864967-37-3
(3R,6aR,10aS,10bR)-6-(methoxycarbonyl)-5-oxo-3-phenyl-2,3,6,6a,7,10,10a,10b-octahydro-5H-oxazolo[2,3-a]isoquinoline

Guidance literature:: Multi-step reaction with 3 steps

1.1: LHMDS

1.2: PhSeCl / tetrahydrofuran

1.3: 86 percent / H₂O₂; pyridine

2.1: 81 percent / LiCl; CuI; TMSCl / tetrahydrofuran

3.1: 85 percent / (1,3-dimesityl-4-imidazolin-2-yl)(PhCH=)RuCl₂(PCy₃) / CH₂Cl₂ / 2 h / 20 °C

With copper(l) iodide; chloro-trimethyl-silane; lithium chloride; lithium hexamethyldisilazane; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol051242c

Reference yield:

: 864967-52-2
(3R,8S,8aR)-8-allyl-6-methoxycarbonyl-5-oxo-3-phenyl-2,3,8,8a-tetrahydro-5H-oxazolo[3,2-a]pyridine

: 864967-37-3
(3R,6aR,10aS,10bR)-6-(methoxycarbonyl)-5-oxo-3-phenyl-2,3,6,6a,7,10,10a,10b-octahydro-5H-oxazolo[2,3-a]isoquinoline

Guidance literature:: Multi-step reaction with 2 steps

1: 81 percent / LiCl; CuI; TMSCl / tetrahydrofuran

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

With copper(l) iodide; chloro-trimethyl-silane; lithium chloride; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol051242c