trans-phenyl 3,4,4a,5,6,8a-hexahydro-4a-(3-methoxyphenyl)-8-methyl-6-oxo-2(1H)-isoquinolinecarboxylate

Base Information

Chemical Name:trans-phenyl 3,4,4a,5,6,8a-hexahydro-4a-(3-methoxyphenyl)-8-methyl-6-oxo-2(1H)-isoquinolinecarboxylate
CAS No.:137517-63-6
Molecular Formula:C₂₄H₂₅NO₄
Molecular Weight:391.467
Hs Code.:

Synonyms:trans-phenyl 3,4,4a,5,6,8a-hexahydro-4a-(3-methoxyphenyl)-8-methyl-6-oxo-2(1H)-isoquinolinecarboxylate

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Chemical Property of trans-phenyl 3,4,4a,5,6,8a-hexahydro-4a-(3-methoxyphenyl)-8-methyl-6-oxo-2(1H)-isoquinolinecarboxylate

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Technology Process of trans-phenyl 3,4,4a,5,6,8a-hexahydro-4a-(3-methoxyphenyl)-8-methyl-6-oxo-2(1H)-isoquinolinecarboxylate

There total 7 articles about trans-phenyl 3,4,4a,5,6,8a-hexahydro-4a-(3-methoxyphenyl)-8-methyl-6-oxo-2(1H)-isoquinolinecarboxylate 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:

: 73224-22-3
1-methyl-4-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine

: 137517-63-6
trans-phenyl 3,4,4a,5,6,8a-hexahydro-4a-(3-methoxyphenyl)-8-methyl-6-oxo-2(1H)-isoquinolinecarboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) n-BuLi, 3.) NaI, K₂CO₃

2: 83 percent / 1.) MeSO₃H, 2.) NaBH₄ / methanol / 1.) from -60 to 25 deg C, 5 min, 2.) RT, 30 min

3: 88 percent / i-Pr₂NEt / 1,2-dichloro-ethane / 1.5 h / Heating

4: 94 percent / OsO₄, NaIO₄ / tetrahydrofuran; H₂O / 4 h / Ambient temperature

5: 1.) PhSeCl, concd HCl, 2.) 30percent H₂O₂, pyridine / 1.) EtOAc, RT, 30 min, 2.) CH₂Cl₂, RT, 45 min

6: 99 percent / CuI / diethyl ether; CH₂Cl₂ / 0.33 h / 0 - 10 °C

7: 1.) PhSeCl, concd HCl, 2.) O₃, 3.) Et₃N, 1-hexene

With pyridine; hydrogenchloride; sodium tetrahydroborate; sodium periodate; copper(l) iodide; osmium(VIII) oxide; n-butyllithium; 1-hexene; Phenylselenyl chloride; methanesulfonic acid; dihydrogen peroxide; potassium carbonate; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane;
DOI:10.1021/jm00079a005

Reference yield:

: trans-decahydro-4a-(3-methoxyphenyl)-2-methyl-6-methyleneisoquinoline

: 137517-63-6
trans-phenyl 3,4,4a,5,6,8a-hexahydro-4a-(3-methoxyphenyl)-8-methyl-6-oxo-2(1H)-isoquinolinecarboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 88 percent / i-Pr₂NEt / 1,2-dichloro-ethane / 1.5 h / Heating

2: 94 percent / OsO₄, NaIO₄ / tetrahydrofuran; H₂O / 4 h / Ambient temperature

3: 1.) PhSeCl, concd HCl, 2.) 30percent H₂O₂, pyridine / 1.) EtOAc, RT, 30 min, 2.) CH₂Cl₂, RT, 45 min

4: 99 percent / CuI / diethyl ether; CH₂Cl₂ / 0.33 h / 0 - 10 °C

5: 1.) PhSeCl, concd HCl, 2.) O₃, 3.) Et₃N, 1-hexene

With pyridine; hydrogenchloride; sodium periodate; copper(l) iodide; osmium(VIII) oxide; 1-hexene; Phenylselenyl chloride; dihydrogen peroxide; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane;
DOI:10.1021/jm00079a005

Reference yield:

: 137517-45-4
2,3,4,4a,5,6,7,8-octahydro-4a-(3-methoxyphenyl)-2-methyl-6-methyleneisoquinoline

: 137517-63-6
trans-phenyl 3,4,4a,5,6,8a-hexahydro-4a-(3-methoxyphenyl)-8-methyl-6-oxo-2(1H)-isoquinolinecarboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: 83 percent / 1.) MeSO₃H, 2.) NaBH₄ / methanol / 1.) from -60 to 25 deg C, 5 min, 2.) RT, 30 min

2: 88 percent / i-Pr₂NEt / 1,2-dichloro-ethane / 1.5 h / Heating

3: 94 percent / OsO₄, NaIO₄ / tetrahydrofuran; H₂O / 4 h / Ambient temperature

4: 1.) PhSeCl, concd HCl, 2.) 30percent H₂O₂, pyridine / 1.) EtOAc, RT, 30 min, 2.) CH₂Cl₂, RT, 45 min

5: 99 percent / CuI / diethyl ether; CH₂Cl₂ / 0.33 h / 0 - 10 °C

6: 1.) PhSeCl, concd HCl, 2.) O₃, 3.) Et₃N, 1-hexene

With pyridine; hydrogenchloride; sodium tetrahydroborate; sodium periodate; copper(l) iodide; osmium(VIII) oxide; 1-hexene; Phenylselenyl chloride; methanesulfonic acid; dihydrogen peroxide; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane;
DOI:10.1021/jm00079a005