(3aS,7aS)-2-[2-(3,4-dimethoxyphenyl)ethyl]-3-hydroxy-1-oxo-octahydro-isoindole-3a-carboxylic acid methyl ester

Base Information

• Chemical Name: (3aS,7aS)-2-[2-(3,4-dimethoxyphenyl)ethyl]-3-hydroxy-1-oxo-octahydro-isoindole-3a-carboxylic acid methyl ester
• CAS No.: 501085-24-1
• Molecular Formula: C₂₀H₂₇NO₆
• Molecular Weight: 377.437
• Mol file: 501085-24-1.mol

Synonyms:

Chemical Property of (3aS,7aS)-2-[2-(3,4-dimethoxyphenyl)ethyl]-3-hydroxy-1-oxo-octahydro-isoindole-3a-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,7aS)-2-[2-(3,4-dimethoxyphenyl)ethyl]-3-hydroxy-1-oxo-octahydro-isoindole-3a-carboxylic acid methyl ester

There total 4 articles about (3aS,7aS)-2-[2-(3,4-dimethoxyphenyl)ethyl]-3-hydroxy-1-oxo-octahydro-isoindole-3a-carboxylic 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:

(3aSR,7aRS)-2-[2-(3,4-dimethoxyphenyl)ethyl]-hexahydro-isoindole-1,3-dione (26478-05-7) → (3aS,7aS)-2-[2-(3,4-dimethoxyphenyl)ethyl]-3-hydroxy-1-oxo-octahydro-isoindole-3a-carboxylic acid methyl ester (501085-24-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: chiral lithium amide base / tetrahydrofuran; hexane / 1.5 h / -78 °C

1.2: 86 percent / tetrahydrofuran; hexane / -78 °C

2.1: 90 percent / NaBH₄ / ethanol / 0.75 h / -5 °C

With sodium tetrahydroborate; chiral lithium amide base; In tetrahydrofuran; ethanol; hexane;

DOI:10.1016/j.tet.2003.08.046

Reference yield:

1,2-cis-cyclohexanedicarboxylic anhydride (13149-00-3) → (3aS,7aS)-2-[2-(3,4-dimethoxyphenyl)ethyl]-3-hydroxy-1-oxo-octahydro-isoindole-3a-carboxylic acid methyl ester (501085-24-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 87 percent / acetic acid / 18 h / Heating

2.1: chiral lithium amide base / tetrahydrofuran; hexane / 1.5 h / -78 °C

2.2: 86 percent / tetrahydrofuran; hexane / -78 °C

3.1: 90 percent / NaBH₄ / ethanol / 0.75 h / -5 °C

With sodium tetrahydroborate; chiral lithium amide base; In tetrahydrofuran; ethanol; hexane; acetic acid;

DOI:10.1016/j.tet.2003.08.046

Reference yield:

2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) → (3aS,7aS)-2-[2-(3,4-dimethoxyphenyl)ethyl]-3-hydroxy-1-oxo-octahydro-isoindole-3a-carboxylic acid methyl ester (501085-24-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 87 percent / AcOH / Heating

2.1: chiral PhCH(Me)NLiCH(Ph)CH(Ph)NHCH(Me)Ph; n-BuLi / tetrahydrofuran; various solvent(s) / 0.5 h / 20 °C

2.2: tetrahydrofuran; various solvent(s) / 1.5 h / -78 °C

2.3: 85.7 percent / tetrahydrofuran; various solvent(s) / 1 h / -78 °C

3.1: 89 percent / NaBH₄ / ethanol / -5 °C

With sodium tetrahydroborate; n-butyllithium; chiral PhCH(Me)NLiCH(Ph)CH(Ph)NHCH(Me)Ph; acetic acid; In tetrahydrofuran; ethanol;

DOI:10.1021/ol027447s

upstream raw materials:

(3aSR,7aRS)-2-[2-(3,4-dimethoxyphenyl)ethyl]-hexahydro-isoindole-1,3-dione

2-(3,4-dimethoxyphenyl)-ethylamine

1,2-cis-cyclohexanedicarboxylic anhydride