Technology Process of 2,3-(R,R)-11b-(S)-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(3-ethyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-α]isoquinoline-2-yl)acetamide
There total 23 articles about 2,3-(R,R)-11b-(S)-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(3-ethyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-α]isoquinoline-2-yl)acetamide which
guide to synthetic route it.
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synthetic route:
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6110-83-4
2,3-(R,R)-11b-(S)-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(3-ethyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-α]isoquinoline-2-yl)acetamide
- Guidance literature:
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2-(3,4-dimethoxyphenyl)-ethylamine;
With
trimethylaluminum;
In
dichloromethane; toluene;
at 25 ℃;
for 1h;
2,3-(R,R)-11b-(S)-(3-ethyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-α]isoquinoline-2-yl)acetic acid methyl ester;
In
dichloromethane; toluene;
for 4.5h;
Heating;
DOI:10.1002/chem.200306039
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6110-83-4
2,3-(R,R)-11b-(S)-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(3-ethyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-α]isoquinoline-2-yl)acetamide
- Guidance literature:
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Multi-step reaction with 4 steps
1.1: CH2Cl2 / 5 h / 20 °C
1.2: 84 percent / pyrrolidine / tetrahydrofuran / 20 °C
2.1: PhLi / tetrahydrofuran; hexane / 5 h
2.2: 57 percent / tetrahydrofuran
3.1: 87 percent / H2 / Pd/C / methanol / 16 h / 20 °C
4.1: 73 percent / AlMe3 / benzene / 10 h / 115 °C
With
hydrogen; trimethylaluminum; phenyllithium;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; hexane; dichloromethane; benzene;
2.1: Wittig reaction;
DOI:10.1021/ol0530326
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6110-83-4
2,3-(R,R)-11b-(S)-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(3-ethyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-α]isoquinoline-2-yl)acetamide
- Guidance literature:
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Multi-step reaction with 6 steps
1.1: 93 percent / second-generation Grubbs' catalyst / CH2Cl2 / 4 h / 60 °C
2.1: 96 percent / TMSOTf / CH2Cl2 / 20 °C
3.1: CH2Cl2 / 5 h / 20 °C
3.2: 84 percent / pyrrolidine / tetrahydrofuran / 20 °C
4.1: PhLi / tetrahydrofuran; hexane / 5 h
4.2: 57 percent / tetrahydrofuran
5.1: 87 percent / H2 / Pd/C / methanol / 16 h / 20 °C
6.1: 73 percent / AlMe3 / benzene / 10 h / 115 °C
With
trimethylsilyl trifluoromethanesulfonate; hydrogen; trimethylaluminum; phenyllithium;
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium on activated charcoal;
In
tetrahydrofuran; methanol; hexane; dichloromethane; benzene;
4.1: Wittig reaction;
DOI:10.1021/ol0530326