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

Base Information

• Chemical Name: (1R)-1-(4-chlorophenyl)-1-[(2S)-2,3-dihydro-1H-indol-2-yl]-2-methoxyethanol
• CAS No.: 849480-04-2
• Molecular Formula: C₁₇H₁₈ClNO₂
• Molecular Weight: 303.788
• Mol file: 849480-04-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (1R)-1-(4-chlorophenyl)-1-[(2S)-2,3-dihydro-1H-indol-2-yl]-2-methoxyethanol 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: 66.0%

tert-butyl (2S)-2-[(1R)-1-(4-chlorophenyl)-1-hydroxy-2-methoxyethyl]indoline-1-carboxylate (849479-95-4) → (1R)-1-(4-chlorophenyl)-1-[(2S)-2,3-dihydro-1H-indol-2-yl]-2-methoxyethanol (849480-04-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/j.tet.2004.12.041

Reference yield:

(S)-indoline-2-carboxylic acid (79815-20-6,78348-24-0) → (1R)-1-(4-chlorophenyl)-1-[(2S)-2,3-dihydro-1H-indol-2-yl]-2-methoxyethanol (849480-04-2)

Guidance literature:

Multi-step reaction with 6 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

6.1: 66 percent / TFA / CH₂Cl₂ / 3 h / 20 °C

With n-butyllithium; sulfuric acid; isopropylmagnesium chloride; trifluoroacetic acid; 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) → (1R)-1-(4-chlorophenyl)-1-[(2S)-2,3-dihydro-1H-indol-2-yl]-2-methoxyethanol (849480-04-2)

Guidance literature:

Multi-step reaction with 5 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

5.1: 66 percent / TFA / CH₂Cl₂ / 3 h / 20 °C

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

DOI:10.1016/j.tet.2004.12.041

upstream raw materials:

tert-butyl (2S)-2-[(1R)-1-(4-chlorophenyl)-1-hydroxy-2-methoxyethyl]indoline-1-carboxylate

(S)-indoline-2-carboxylic acid

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

methyl (S)-N-(tert-butoxycarbonyl)indoline-2-carboxylate