trans-4a-(2,3-dimethoxyphenyl)-2-methyl-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline

Base Information

Chemical Name:trans-4a-(2,3-dimethoxyphenyl)-2-methyl-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline
CAS No.:81012-15-9
Molecular Formula:C₁₈H₂₅NO₃
Molecular Weight:303.401
Hs Code.:

Synonyms:trans-4a-(2,3-dimethoxyphenyl)-2-methyl-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline

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Chemical Property of trans-4a-(2,3-dimethoxyphenyl)-2-methyl-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline

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Technology Process of trans-4a-(2,3-dimethoxyphenyl)-2-methyl-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline

There total 7 articles about trans-4a-(2,3-dimethoxyphenyl)-2-methyl-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline 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: 92.0%

: 81012-14-8
trans-4a-(2,3-dimethoxyphenyl)-6,6-(ethylenedioxy)-2-methyl-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline

: 81012-15-9
trans-4a-(2,3-dimethoxyphenyl)-2-methyl-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline

Guidance literature:: With sulfuric acid; In tetrahydrofuran; for 20h; Ambient temperature;
DOI:10.1021/jo00349a006

Reference yield:

: 79619-11-7
4-(Carboxymethyl)-4-(2,3-dimethoxyphenyl)-1-methyl-3-methylene-2-piperidinone

: 81012-15-9
trans-4a-(2,3-dimethoxyphenyl)-2-methyl-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline

Guidance literature:: Multi-step reaction with 7 steps

1: 98 percent / CH₂Cl₂ / 9.5 h / Ambient temperature

2: 1.) isopropylmagnesium bromide / 1.) THF, RT, 4 h, and reflux, 45 min, 2.) THF, RT, 3 d

3: 98 percent / NaOMe / methanol / 20 h / Ambient temperature

4: 1.) trifluoroacetic acid / 1.) CH₂Cl₂, RT, 35 min, 2.) toluene, reflux, 7 min

5: 70 percent / p-toluenesulfonic acid monohydrate / benzene / Heating

6: 1.) AlH₃, MeOH, 2.) NaBH₄ / 1.) THF, 0 deg C, 12 min, 2.) EtOH, 0 deg C, 18 h

7: 92 percent / aq. H₂SO₄ / tetrahydrofuran / 20 h / Ambient temperature

With aluminium hydride; methanol; sodium tetrahydroborate; sulfuric acid; isopropylmagnesium bromide; toluene-4-sulfonic acid; trifluoroacetic acid; sodium methylate; In tetrahydrofuran; methanol; dichloromethane; benzene;
DOI:10.1021/jo00349a006

Reference yield:

: 81012-10-4
imidazolide of 4-(carboxymethyl)-4-(2,3-dimethoxyphenyl)-1-methyl-3-methylene-2-piperidinone

: 81012-15-9
trans-4a-(2,3-dimethoxyphenyl)-2-methyl-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) isopropylmagnesium bromide / 1.) THF, RT, 4 h, and reflux, 45 min, 2.) THF, RT, 3 d

2: 98 percent / NaOMe / methanol / 20 h / Ambient temperature

3: 1.) trifluoroacetic acid / 1.) CH₂Cl₂, RT, 35 min, 2.) toluene, reflux, 7 min

4: 70 percent / p-toluenesulfonic acid monohydrate / benzene / Heating

5: 1.) AlH₃, MeOH, 2.) NaBH₄ / 1.) THF, 0 deg C, 12 min, 2.) EtOH, 0 deg C, 18 h

6: 92 percent / aq. H₂SO₄ / tetrahydrofuran / 20 h / Ambient temperature

With aluminium hydride; methanol; sodium tetrahydroborate; sulfuric acid; isopropylmagnesium bromide; toluene-4-sulfonic acid; trifluoroacetic acid; sodium methylate; In tetrahydrofuran; methanol; benzene;
DOI:10.1021/jo00349a006