1H-Indole-1-carboxylic acid, 2-[(1R)-1-(4-chlorophenyl)-1-hydroxy-2-methoxyethyl]-2,3-dihydro-, 1,1-dimethylethyl ester, (2S)-

Base Information

• Chemical Name: 1H-Indole-1-carboxylic acid, 2-[(1R)-1-(4-chlorophenyl)-1-hydroxy-2-methoxyethyl]-2,3-dihydro-, 1,1-dimethylethyl ester, (2S)-
• CAS No.: 849479-95-4
• Molecular Formula: C22H26ClNO4
• Molecular Weight: 403.906
• Mol file: 849479-95-4.mol

Synonyms:

Chemical Property of 1H-Indole-1-carboxylic acid, 2-[(1R)-1-(4-chlorophenyl)-1-hydroxy-2-methoxyethyl]-2,3-dihydro-, 1,1-dimethylethyl ester, (2S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1H-Indole-1-carboxylic acid, 2-[(1R)-1-(4-chlorophenyl)-1-hydroxy-2-methoxyethyl]-2,3-dihydro-, 1,1-dimethylethyl ester, (2S)-

There total 5 articles about 1H-Indole-1-carboxylic acid, 2-[(1R)-1-(4-chlorophenyl)-1-hydroxy-2-methoxyethyl]-2,3-dihydro-, 1,1-dimethylethyl ester, (2S)- 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: 61.0%

(4-chlorphenyl)magnesium bromide (873-77-8) + tert-butyl (2S)-2-(methoxyacetyl)indoline-1-carboxylate (500548-61-8) → (S)-2-[(S)-1-(4-Chloro-phenyl)-1-hydroxy-2-methoxy-ethyl]-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester + tert-butyl (2S)-2-[(1R)-1-(4-chlorophenyl)-1-hydroxy-2-methoxyethyl]indoline-1-carboxylate (849479-95-4)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 0.25h;

DOI:10.1016/j.tet.2004.12.041

Reference yield:

(S)-indoline-2-carboxylic acid (79815-20-6,78348-24-0) → tert-butyl (2S)-2-[(1R)-1-(4-chlorophenyl)-1-hydroxy-2-methoxyethyl]indoline-1-carboxylate (849479-95-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sulfuric acid / 6 h / 80 °C

2.1: 31.4 g / CH₂Cl₂ / 20 °C

3.1: 72 percent / i-propylmagnesium chloride / tetrahydrofuran / 0.5 h / -10 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

4.2: 56 percent / tetrahydrofuran; hexane / 0.25 h / -78 °C

5.1: 61 percent / tetrahydrofuran / 0.25 h / -78 °C

With n-butyllithium; sulfuric acid; isopropylmagnesium chloride; In tetrahydrofuran; hexane; dichloromethane; 5.1: Grignard addition;

DOI:10.1016/j.tet.2004.12.041

Reference yield:

(S)-indoline-2-carboxylic acid methyl ester (141410-06-2) → tert-butyl (2S)-2-[(1R)-1-(4-chlorophenyl)-1-hydroxy-2-methoxyethyl]indoline-1-carboxylate (849479-95-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 31.4 g / CH₂Cl₂ / 20 °C

2.1: 72 percent / i-propylmagnesium chloride / tetrahydrofuran / 0.5 h / -10 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

3.2: 56 percent / tetrahydrofuran; hexane / 0.25 h / -78 °C

4.1: 61 percent / tetrahydrofuran / 0.25 h / -78 °C

With n-butyllithium; isopropylmagnesium chloride; In tetrahydrofuran; hexane; dichloromethane; 4.1: Grignard addition;

DOI:10.1016/j.tet.2004.12.041

upstream raw materials:

(4-chlorphenyl)magnesium bromide

tert-butyl (2S)-2-(methoxyacetyl)indoline-1-carboxylate

(S)-indoline-2-carboxylic acid

(S)-indoline-2-carboxylic acid methyl ester

Downstream raw materials:

(1R)-1-(4-chlorophenyl)-1-[(2S)-2,3-dihydro-1H-indol-2-yl]-2-methoxyethanol