2,2-Dimethyl-propionic acid (3aR,7aS)-3a-(3,4-dimethoxy-phenyl)-1-methyl-6-oxo-octahydro-indol-5-yl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (3aR,7aS)-3a-(3,4-dimethoxy-phenyl)-1-methyl-6-oxo-octahydro-indol-5-yl ester
• CAS No.: 131652-83-0
• Molecular Formula: C₂₂H₃₁NO₅
• Molecular Weight: 389.492
• Mol file: 131652-83-0.mol

Synonyms:

Chemical Property of 2,2-Dimethyl-propionic acid (3aR,7aS)-3a-(3,4-dimethoxy-phenyl)-1-methyl-6-oxo-octahydro-indol-5-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (3aR,7aS)-3a-(3,4-dimethoxy-phenyl)-1-methyl-6-oxo-octahydro-indol-5-yl ester

There total 13 articles about 2,2-Dimethyl-propionic acid (3aR,7aS)-3a-(3,4-dimethoxy-phenyl)-1-methyl-6-oxo-octahydro-indol-5-yl 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: 49.0%

2,2-Dimethyl-propionic acid (3aR,7aS)-6-benzyloxy-3a-(3,4-dimethoxy-phenyl)-1-methyl-2,3,3a,4,5,7a-hexahydro-1H-indol-5-yl ester (131652-86-3,131652-87-4) → 2,2-Dimethyl-propionic acid (3aR,7aS)-3a-(3,4-dimethoxy-phenyl)-1-methyl-6-oxo-octahydro-indol-5-yl ester (131652-83-0,131653-05-9)

Guidance literature:

With hydrogenchloride; In ethanol; at 60 ℃; for 2h;

DOI:10.1246/cl.1990.1239

Reference yield:

(R)-5-Benzyloxy-2-(3,4-dimethoxy-phenyl)-pentane-1,4-diol (131652-78-3,131723-78-9) → 2,2-Dimethyl-propionic acid (3aR,7aS)-3a-(3,4-dimethoxy-phenyl)-1-methyl-6-oxo-octahydro-indol-5-yl ester (131652-83-0,131653-05-9)

Guidance literature:

Multi-step reaction with 12 steps

1: 94 percent / n-Bu₃P / tetrahydrofuran / 1 h / Ambient temperature

2: Et₃N / CH₂Cl₂ / 0.5 h / -10 °C

3: CH₂Cl₂ / 5 h / Ambient temperature

4: 100 percent / 30percent H₂O₂ / CH₂Cl₂ / 9 h / 0 deg C to r.t.

5: 85 percent / xylene / 0.33 h / 250 °C / sealed tube

6: 88 percent / H₂ / 20percent Pd(OH)2-C / methanol / 8 h / Ambient temperature

7: 2) NaBH₄ / 1) MeOH, O deg C, 1h, 2) O deg C to r.t.

8: 1) oxalyl chloride, 2) Et₃N / 1) CH₂Cl₂, -71 deg C, 1.5 h, 2) -71 deg C to r.t.

9: 0.5 N NaOH / ethanol / 11 h / Ambient temperature

10: CeCl₃*7H₂O, NaBH₄ / methanol / 1.5 h / 0 °C

11: Et₃N / DMAP / CH₂Cl₂ / 12 h / Ambient temperature

12: 49 percent / 6N HCl / ethanol / 2 h / 60 °C

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; tributylphosphine; hydrogen; dihydrogen peroxide; triethylamine; dmap; palladium hydroxide - carbon; In tetrahydrofuran; methanol; ethanol; dichloromethane; xylene;

DOI:10.1246/cl.1990.1239

Reference yield:

(R)-5-Benzyloxymethyl-3-(3,4-dimethoxy-phenyl)-dihydro-furan-2-one (81309-80-0,81309-81-1) → 2,2-Dimethyl-propionic acid (3aR,7aS)-3a-(3,4-dimethoxy-phenyl)-1-methyl-6-oxo-octahydro-indol-5-yl ester (131652-83-0,131653-05-9)

Guidance literature:

Multi-step reaction with 13 steps

1: 97 percent / LiAlH₄ / tetrahydrofuran / 0.67 h / 0 °C

2: 94 percent / n-Bu₃P / tetrahydrofuran / 1 h / Ambient temperature

3: Et₃N / CH₂Cl₂ / 0.5 h / -10 °C

4: CH₂Cl₂ / 5 h / Ambient temperature

5: 100 percent / 30percent H₂O₂ / CH₂Cl₂ / 9 h / 0 deg C to r.t.

6: 85 percent / xylene / 0.33 h / 250 °C / sealed tube

7: 88 percent / H₂ / 20percent Pd(OH)2-C / methanol / 8 h / Ambient temperature

8: 2) NaBH₄ / 1) MeOH, O deg C, 1h, 2) O deg C to r.t.

9: 1) oxalyl chloride, 2) Et₃N / 1) CH₂Cl₂, -71 deg C, 1.5 h, 2) -71 deg C to r.t.

10: 0.5 N NaOH / ethanol / 11 h / Ambient temperature

11: CeCl₃*7H₂O, NaBH₄ / methanol / 1.5 h / 0 °C

12: Et₃N / DMAP / CH₂Cl₂ / 12 h / Ambient temperature

13: 49 percent / 6N HCl / ethanol / 2 h / 60 °C

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; cerium(III) chloride; oxalyl dichloride; tributylphosphine; hydrogen; dihydrogen peroxide; triethylamine; dmap; palladium hydroxide - carbon; In tetrahydrofuran; methanol; ethanol; dichloromethane; xylene;

DOI:10.1246/cl.1990.1239

upstream raw materials:

2,2-Dimethyl-propionic acid (3aR,7aS)-6-benzyloxy-3a-(3,4-dimethoxy-phenyl)-1-methyl-2,3,3a,4,5,7a-hexahydro-1H-indol-5-yl ester

(R)-5-Benzyloxy-2-(3,4-dimethoxy-phenyl)-pentane-1,4-diol

(R)-5-Benzyloxymethyl-3-(3,4-dimethoxy-phenyl)-dihydro-furan-2-one

(R)-1-Benzyloxy-3-[(2R,3R)-3-(3,4-dimethoxy-phenyl)-2-hydroxymethyl-1-methyl-pyrrolidin-3-yl]-propan-2-ol

Downstream raw materials:

(-)-mesembrine

Refernces