(S)-4-(3,4-Dimethoxy-phenyl)-4-(2-hydroxy-ethyl)-3-methylamino-cyclohex-2-enone

Base Information

Chemical Name:(S)-4-(3,4-Dimethoxy-phenyl)-4-(2-hydroxy-ethyl)-3-methylamino-cyclohex-2-enone
CAS No.:81369-83-7
Molecular Formula:C₁₇H₂₃NO₄
Molecular Weight:305.374
Hs Code.:

Synonyms:(S)-4-(3,4-Dimethoxy-phenyl)-4-(2-hydroxy-ethyl)-3-methylamino-cyclohex-2-enone

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Chemical Property of (S)-4-(3,4-Dimethoxy-phenyl)-4-(2-hydroxy-ethyl)-3-methylamino-cyclohex-2-enone

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Technology Process of (S)-4-(3,4-Dimethoxy-phenyl)-4-(2-hydroxy-ethyl)-3-methylamino-cyclohex-2-enone

There total 9 articles about (S)-4-(3,4-Dimethoxy-phenyl)-4-(2-hydroxy-ethyl)-3-methylamino-cyclohex-2-enone 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: 41.0%

: 81369-82-6
(S)-3a-(3,4-Dimethoxy-phenyl)-3,3a,4,5-tetrahydro-2H-benzofuran-6-one

: 74-89-5
methylamine

: 35714-44-4
Δ7-mesembrenone

: 81369-83-7
(S)-4-(3,4-Dimethoxy-phenyl)-4-(2-hydroxy-ethyl)-3-methylamino-cyclohex-2-enone

Guidance literature:: In water; at 180 ℃; for 1h; sealed tube;
DOI:10.1016/S0040-4039(01)93019-9

Reference yield:

: 93-17-4
3,4-dimethoxyphenylacetonitrile

: 81369-83-7
(S)-4-(3,4-Dimethoxy-phenyl)-4-(2-hydroxy-ethyl)-3-methylamino-cyclohex-2-enone

Guidance literature:: Multi-step reaction with 9 steps

1: LDA / tetrahydrofuran / -78 - 20 °C

2: 1.) 10percent KOH-EtOH, 2.) 10percent HCl-EtOH / 1.) reflux over night, 2.) room temperature

3: 1.) lithium diisopropylamide / tetrahydrofuran / from -78 degC up to room temperature

4: c.HCl / ethanol / 3 h / Heating

6: 1.) NaBH₄, 2.) acid

7: 73 percent / O₂ / PdCl₂-CuCl / dimethylformamide / 168 h

8: 66 percent / tetrahydrofuran / Heating

9: 41 percent / H₂O / 1 h / 180 °C / sealed tube

With hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; oxygen; lithium diisopropyl amide; copper(l) chloride; palladium dichloride; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(01)93019-9

Reference yield:

: 81309-80-0,81309-81-1
(R)-5-Benzyloxymethyl-3-(3,4-dimethoxy-phenyl)-dihydro-furan-2-one

: 81369-83-7
(S)-4-(3,4-Dimethoxy-phenyl)-4-(2-hydroxy-ethyl)-3-methylamino-cyclohex-2-enone

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) lithium diisopropylamide / tetrahydrofuran / from -78 degC up to room temperature

2: c.HCl / ethanol / 3 h / Heating

4: 1.) NaBH₄, 2.) acid

5: 73 percent / O₂ / PdCl₂-CuCl / dimethylformamide / 168 h

6: 66 percent / tetrahydrofuran / Heating

7: 41 percent / H₂O / 1 h / 180 °C / sealed tube

With hydrogenchloride; sodium tetrahydroborate; oxygen; lithium diisopropyl amide; copper(l) chloride; palladium dichloride; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(01)93019-9