(4aR,8aS)-8a-(hydroxymethyl)-2-[(1R)-2-hydroxy-1-phenylethyl]-6,7-dimethyl-2,3,4,4a,5,8-hexahydro-1H-isoquinoline

Base Information

Chemical Name:(4aR,8aS)-8a-(hydroxymethyl)-2-[(1R)-2-hydroxy-1-phenylethyl]-6,7-dimethyl-2,3,4,4a,5,8-hexahydro-1H-isoquinoline
CAS No.:602302-29-4
Molecular Formula:C₂₀H₂₉NO₂
Molecular Weight:315.456
Hs Code.:

Synonyms:(4aR,8aS)-8a-(hydroxymethyl)-2-[(1R)-2-hydroxy-1-phenylethyl]-6,7-dimethyl-2,3,4,4a,5,8-hexahydro-1H-isoquinoline

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Chemical Property of (4aR,8aS)-8a-(hydroxymethyl)-2-[(1R)-2-hydroxy-1-phenylethyl]-6,7-dimethyl-2,3,4,4a,5,8-hexahydro-1H-isoquinoline

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Technology Process of (4aR,8aS)-8a-(hydroxymethyl)-2-[(1R)-2-hydroxy-1-phenylethyl]-6,7-dimethyl-2,3,4,4a,5,8-hexahydro-1H-isoquinoline

There total 4 articles about (4aR,8aS)-8a-(hydroxymethyl)-2-[(1R)-2-hydroxy-1-phenylethyl]-6,7-dimethyl-2,3,4,4a,5,8-hexahydro-1H-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: 67.0%

: 602302-19-2
(3R,5aR,9aS,10aS)-5a-(methoxycarbonyl)-7,8-dimethyl-5-oxo-3-phenyl-2,3,9,9a,10,10a-hexahydro-6H-oxazolo[3,2-b]isoquinoline

: 602302-29-4
(4aR,8aS)-8a-(hydroxymethyl)-2-[(1R)-2-hydroxy-1-phenylethyl]-6,7-dimethyl-2,3,4,4a,5,8-hexahydro-1H-isoquinoline

Guidance literature:: With lithium aluminium tetrahydride; aluminium trichloride; In tetrahydrofuran; at -78 - 20 ℃;
DOI:10.1016/S0957-4166(03)00368-9

Reference yield:

: 513-81-5
2,3-dimethyl-buta-1,3-diene

: 602302-29-4
(4aR,8aS)-8a-(hydroxymethyl)-2-[(1R)-2-hydroxy-1-phenylethyl]-6,7-dimethyl-2,3,4,4a,5,8-hexahydro-1H-isoquinoline

Guidance literature:: Multi-step reaction with 2 steps

1: 184 mg / ZnBr₂ / CH₂Cl₂ / 4.5 h / 20 °C

2: 67 percent / LiAlH₄; AlCl₃ / tetrahydrofuran / -78 - 20 °C

With lithium aluminium tetrahydride; aluminium trichloride; zinc dibromide; In tetrahydrofuran; dichloromethane; 1: Diels-Alder reaction;
DOI:10.1016/S0957-4166(03)00368-9

Reference yield:

: 602307-00-6
(3R,8aS)-6-(methoxycarbonyl)-5-oxo-3-phenyl-6-(phenylselanyl)-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

: 602302-29-4
(4aR,8aS)-8a-(hydroxymethyl)-2-[(1R)-2-hydroxy-1-phenylethyl]-6,7-dimethyl-2,3,4,4a,5,8-hexahydro-1H-isoquinoline

Guidance literature:: Multi-step reaction with 3 steps

1.1: O₃ / CH₂Cl₂ / 0.5 h / -78 °C

1.2: 348 mg / O₂ / CH₂Cl₂ / -78 - 25 °C

2.1: 184 mg / ZnBr₂ / CH₂Cl₂ / 4.5 h / 20 °C

3.1: 67 percent / LiAlH₄; AlCl₃ / tetrahydrofuran / -78 - 20 °C

With lithium aluminium tetrahydride; aluminium trichloride; ozone; zinc dibromide; In tetrahydrofuran; dichloromethane; 2.1: Diels-Alder reaction;
DOI:10.1016/S0957-4166(03)00368-9