(4aα,8α,8aβ)-2-(cyclopropylmethyl)decahydro-4a-(3-methoxyphenyl)-8-methyl-6-methyleneisoquinoline

Base Information

Chemical Name:(4aα,8α,8aβ)-2-(cyclopropylmethyl)decahydro-4a-(3-methoxyphenyl)-8-methyl-6-methyleneisoquinoline
CAS No.:137517-66-9
Molecular Formula:C₂₂H₃₁NO
Molecular Weight:325.494
Hs Code.:

Synonyms:(4aα,8α,8aβ)-2-(cyclopropylmethyl)decahydro-4a-(3-methoxyphenyl)-8-methyl-6-methyleneisoquinoline

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (4aα,8α,8aβ)-2-(cyclopropylmethyl)decahydro-4a-(3-methoxyphenyl)-8-methyl-6-methyleneisoquinoline

Chemical Property:

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Technology Process of (4aα,8α,8aβ)-2-(cyclopropylmethyl)decahydro-4a-(3-methoxyphenyl)-8-methyl-6-methyleneisoquinoline

There total 11 articles about (4aα,8α,8aβ)-2-(cyclopropylmethyl)decahydro-4a-(3-methoxyphenyl)-8-methyl-6-methyleneisoquinoline 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: 45.0%

: 137517-67-0
(4aα,8α,8aβ)-decahydro-4a-(3-methoxyphenyl)-8-methyl-6-methyleneisoquinoline

: 7051-34-5
cyclopropylcarbinyl bromide

: 137517-66-9
(4aα,8α,8aβ)-2-(cyclopropylmethyl)decahydro-4a-(3-methoxyphenyl)-8-methyl-6-methyleneisoquinoline

Guidance literature:: With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 150 ℃; for 4h;
DOI:10.1021/jm00079a005

Reference yield:

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

: 137517-66-9
(4aα,8α,8aβ)-2-(cyclopropylmethyl)decahydro-4a-(3-methoxyphenyl)-8-methyl-6-methyleneisoquinoline

Guidance literature:: Multi-step reaction with 11 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

8: 75 percent / H₂ / 10percent Pd/C / ethanol / 19 h / 760 Torr / Ambient temperature

9: 1.) TiCl₄, Zn / 1.) THF, 4 deg C, 3 d, 2.) THF, CH₂Cl₂, 0 deg C, 30 min

10: 85 percent / 50percent aq. KOH / ethanol / 17 h / Heating

11: 45 percent / NaHCO₃ / dimethylformamide / 4 h / 150 °C

With pyridine; hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; sodium periodate; copper(l) iodide; osmium(VIII) oxide; n-butyllithium; 1-hexene; Phenylselenyl chloride; methanesulfonic acid; hydrogen; dihydrogen peroxide; titanium tetrachloride; sodium hydrogencarbonate; potassium carbonate; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00079a005

Reference yield:

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

: 137517-66-9
(4aα,8α,8aβ)-2-(cyclopropylmethyl)decahydro-4a-(3-methoxyphenyl)-8-methyl-6-methyleneisoquinoline

Guidance literature:: Multi-step reaction with 9 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

6: 75 percent / H₂ / 10percent Pd/C / ethanol / 19 h / 760 Torr / Ambient temperature

7: 1.) TiCl₄, Zn / 1.) THF, 4 deg C, 3 d, 2.) THF, CH₂Cl₂, 0 deg C, 30 min

8: 85 percent / 50percent aq. KOH / ethanol / 17 h / Heating

9: 45 percent / NaHCO₃ / dimethylformamide / 4 h / 150 °C

With pyridine; hydrogenchloride; potassium hydroxide; sodium periodate; copper(l) iodide; osmium(VIII) oxide; 1-hexene; Phenylselenyl chloride; hydrogen; dihydrogen peroxide; titanium tetrachloride; sodium hydrogencarbonate; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00079a005