(7R,8S)-8-(3,4-DiMethoxyphenyl)-8-(2-propen-1-yl)-1,4-dioxaspiro[4.5]decan-7-ol

Base Information

• Chemical Name: (7R,8S)-8-(3,4-DiMethoxyphenyl)-8-(2-propen-1-yl)-1,4-dioxaspiro[4.5]decan-7-ol
• CAS No.: 866394-48-1
• Molecular Formula: C₁₉H₂₆O₅
• Molecular Weight: 334.412
• Mol file: 866394-48-1.mol

Synonyms:(7R,8S)-8-Allyl-8-(3,4-dimethoxy-phenyl)-1,4-dioxa-spiro[4.5]decan-7-ol

Chemical Property of (7R,8S)-8-(3,4-DiMethoxyphenyl)-8-(2-propen-1-yl)-1,4-dioxaspiro[4.5]decan-7-ol

Chemical Property:

• Boiling Point: 477.2±45.0 °C(Predicted)
• PKA: 14.89±0.40(Predicted)
• Density: 1.18±0.1 g/cm3(Predicted)
• Solubility.: Chloroform, Ethyl Acetate

Purity/Quality:

(7R,8S)-8-(3,4-Dimethoxyphenyl)-8-(2-propen-1-yl)-1,4-dioxaspiro[4.5]decan-7-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (7R,8S)-8-(3,4-Dimethoxyphenyl)-8-(2-propen-1-yl)-1,4-dioxaspiro[4.5]decan-7-ol is an intermediate in the synthesis of Mesembrine (M338950), a serotonin-uptake inhibitor which occurs naturally as the (-)-form.

Technology Process of (7R,8S)-8-(3,4-DiMethoxyphenyl)-8-(2-propen-1-yl)-1,4-dioxaspiro[4.5]decan-7-ol

There total 4 articles about (7R,8S)-8-(3,4-DiMethoxyphenyl)-8-(2-propen-1-yl)-1,4-dioxaspiro[4.5]decan-7-ol 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%

allylmagnesium bromide (2622-05-1) + 4,4-ethylenedioxy-1-(3',4'-dimethoxyphenyl)cyclohexene (70779-49-6) → (7S,8R)-8-Allyl-8-(3,4-dimethoxy-phenyl)-1,4-dioxa-spiro[4.5]decan-7-ol + (7R,8S)-8-Allyl-8-(3,4-dimethoxy-phenyl)-1,4-dioxa-spiro[4.5]decan-7-ol (866394-48-1)

Guidance literature:

4,4-ethylenedioxy-1-(3',4'-dimethoxyphenyl)cyclohexene; With Oxone; Shi's ketone; tetra(n-butyl)ammonium hydrogensulfate; potassium hydroxide; disodium ethylenediaminetetraacetic acid; In dichloromethane; water; acetonitrile; at 0 ℃; for 4h;

allylmagnesium bromide; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/jo0511039

Reference yield:

cyclohexanedione monoethylene ketal (4746-97-8) → (7R,8S)-8-Allyl-8-(3,4-dimethoxy-phenyl)-1,4-dioxa-spiro[4.5]decan-7-ol (866394-48-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: magnesium / tetrahydrofuran

1.2: tetrahydrofuran / 0 - 20 °C

2.1: 8.86 g / p-toluenesulfonic acid / ethane-1,2-diol; benzene / Heating

3.1: Shi's chiral ketone; oxone; tetrabutylammonium hydrogen sulfate / ethylenediaminetetraacetic acid disodium salt; potassium hydroxide / CH₂Cl₂; acetonitrile; H₂O / 4 h / 0 °C

3.2: 73 percent / tetrahydrofuran / 0 - 20 °C

With Oxone; Shi's ketone; tetra(n-butyl)ammonium hydrogensulfate; toluene-4-sulfonic acid; magnesium; potassium hydroxide; disodium ethylenediaminetetraacetic acid; In tetrahydrofuran; dichloromethane; water; ethylene glycol; acetonitrile; benzene; 1.2: Grignard reaction / 3.1: Shi epoxidation / 3.2: Grignard reaction;

DOI:10.1021/jo0511039

Reference yield:

4-Bromoveratrole (2859-78-1) → (7R,8S)-8-Allyl-8-(3,4-dimethoxy-phenyl)-1,4-dioxa-spiro[4.5]decan-7-ol (866394-48-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: magnesium / tetrahydrofuran

1.2: tetrahydrofuran / 0 - 20 °C

2.1: 8.86 g / p-toluenesulfonic acid / ethane-1,2-diol; benzene / Heating

3.1: Shi's chiral ketone; oxone; tetrabutylammonium hydrogen sulfate / ethylenediaminetetraacetic acid disodium salt; potassium hydroxide / CH₂Cl₂; acetonitrile; H₂O / 4 h / 0 °C

3.2: 73 percent / tetrahydrofuran / 0 - 20 °C

With Oxone; Shi's ketone; tetra(n-butyl)ammonium hydrogensulfate; toluene-4-sulfonic acid; magnesium; potassium hydroxide; disodium ethylenediaminetetraacetic acid; In tetrahydrofuran; dichloromethane; water; ethylene glycol; acetonitrile; benzene; 1.2: Grignard reaction / 3.1: Shi epoxidation / 3.2: Grignard reaction;

DOI:10.1021/jo0511039

upstream raw materials:

allylmagnesium bromide

4,4-ethylenedioxy-1-(3',4'-dimethoxyphenyl)cyclohexene

cyclohexanedione monoethylene ketal

4-Bromoveratrole

Downstream raw materials:

(4R)-4-(3,4-dimethoxyphenyl)-4-(2-hydroxyethyl)cyclohex-2-enole

(-)-mesembrine

(R)-4-(3,4-Dimethoxy-phenyl)-4-(2-methylamino-ethyl)-cyclohex-2-enol

Toluene-4-sulfonic acid 2-[(R)-1-(3,4-dimethoxy-phenyl)-4-hydroxy-cyclohex-2-enyl]-ethyl ester