{2-[(R)-1-(3,4-Dimethoxy-phenyl)-4-oxo-cyclohex-2-enyl]-ethyl}-methyl-carbamic acid methyl ester

Base Information

• Chemical Name: {2-[(R)-1-(3,4-Dimethoxy-phenyl)-4-oxo-cyclohex-2-enyl]-ethyl}-methyl-carbamic acid methyl ester
• CAS No.: 216005-93-5
• Molecular Formula: C₁₉H₂₅NO₅
• Molecular Weight: 347.411

Synonyms:{2-[(R)-1-(3,4-Dimethoxy-phenyl)-4-oxo-cyclohex-2-enyl]-ethyl}-methyl-carbamic acid methyl ester

Chemical Property of {2-[(R)-1-(3,4-Dimethoxy-phenyl)-4-oxo-cyclohex-2-enyl]-ethyl}-methyl-carbamic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {2-[(R)-1-(3,4-Dimethoxy-phenyl)-4-oxo-cyclohex-2-enyl]-ethyl}-methyl-carbamic acid methyl ester

There total 35 articles about {2-[(R)-1-(3,4-Dimethoxy-phenyl)-4-oxo-cyclohex-2-enyl]-ethyl}-methyl-carbamic acid methyl ester 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: 73.0%

{2-[(R)-1-(3,4-Dimethoxy-phenyl)-cyclohex-2-enyl]-ethyl}-methyl-carbamic acid methyl ester (216005-92-4) → {2-[(R)-1-(3,4-Dimethoxy-phenyl)-4-oxo-cyclohex-2-enyl]-ethyl}-methyl-carbamic acid methyl ester (216005-93-5)

Guidance literature:

With 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; In dichloromethane; at -15 ℃; for 2h;

DOI:10.1016/S0040-4039(98)01689-X

Reference yield:

4-Bromoveratrole (2859-78-1) → {2-[(R)-1-(3,4-Dimethoxy-phenyl)-4-oxo-cyclohex-2-enyl]-ethyl}-methyl-carbamic acid methyl ester (216005-93-5)

Guidance literature:

Multi-step reaction with 15 steps

1: 80 percent / butyllithium / tetrahydrofuran / -78 °C

2: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran

3: pyridinium chlorochromate; NaOAc

4: acetic acid / 40 °C

5: 98 percent / NaBH₄; CeCl₃*7H₂O / methanol / -20 °C

6: 76 percent / decahydronaphthalene / 220 °C

7: H₂ / Pd-C / ethyl acetate

8: p-TsOH / methanol / Heating

9: 88 percent / Dess-Martin periodinane / CH₂Cl₂

10: CeCl₃ / tetrahydrofuran / -20 °C

11: Me₃Al / tetrahydrofuran / Heating

12: LiAlH₄ / dioxane / Heating

13: Huenig base / CH₂Cl₂

14: NaIO₄ / tetrahydrofuran; H₂O

15: KOH / methanol

With potassium hydroxide; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; cerium(III) chloride; tetrabutyl ammonium fluoride; hydrogen; trimethylaluminum; sodium acetate; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; acetic acid; ethyl acetate; decalin; 6: Eschenmoser reaction;

DOI:10.1016/S0040-4039(02)00033-3

Reference yield:

(3aS,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-one (288269-05-6) → {2-[(R)-1-(3,4-Dimethoxy-phenyl)-4-oxo-cyclohex-2-enyl]-ethyl}-methyl-carbamic acid methyl ester (216005-93-5)

Guidance literature:

Multi-step reaction with 15 steps

1: 80 percent / butyllithium / tetrahydrofuran / -78 °C

2: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran

3: pyridinium chlorochromate; NaOAc

4: acetic acid / 40 °C

5: 98 percent / NaBH₄; CeCl₃*7H₂O / methanol / -20 °C

6: 76 percent / decahydronaphthalene / 220 °C

7: H₂ / Pd-C / ethyl acetate

8: p-TsOH / methanol / Heating

9: 88 percent / Dess-Martin periodinane / CH₂Cl₂

10: CeCl₃ / tetrahydrofuran / -20 °C

11: Me₃Al / tetrahydrofuran / Heating

12: LiAlH₄ / dioxane / Heating

13: Huenig base / CH₂Cl₂

14: NaIO₄ / tetrahydrofuran; H₂O

15: KOH / methanol

With potassium hydroxide; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; cerium(III) chloride; tetrabutyl ammonium fluoride; hydrogen; trimethylaluminum; sodium acetate; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; acetic acid; ethyl acetate; decalin; 6: Eschenmoser reaction;

DOI:10.1016/S0040-4039(02)00033-3

upstream raw materials:

{2-[(R)-1-(3,4-Dimethoxy-phenyl)-cyclohex-2-enyl]-ethyl}-methyl-carbamic acid methyl ester

[(S)-3-(3,4-Dimethoxy-phenyl)-3-formyl-6-oxo-heptyl]-methyl-carbamic acid methyl ester

4-Bromoveratrole

(3aS,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-one

Downstream raw materials:

(-)-mesembrine

{2-[(R)-1-(3,4-Dimethoxy-phenyl)-3-iodo-4-oxo-cyclohex-2-enyl]-ethyl}-methyl-carbamic acid methyl ester

{2-[(S)-6-(3,4-Dimethoxy-phenyl)-5,6,7,8-tetrahydro-quinolin-6-yl]-ethyl}-methyl-amine

{2-[(S)-6-(3,4-Dimethoxy-phenyl)-5,6,7,8-tetrahydro-quinolin-6-yl]-ethyl}-methyl-carbamic acid methyl ester

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