(R)-2-((S)-5-Bromo-2,3-dihydro-1H-indol-2-yl)-1-methoxy-4-phenyl-butan-2-ol

Base Information

Chemical Name:(R)-2-((S)-5-Bromo-2,3-dihydro-1H-indol-2-yl)-1-methoxy-4-phenyl-butan-2-ol
CAS No.:849480-33-7
Molecular Formula:C₁₉H₂₂BrNO₂
Molecular Weight:376.293
Hs Code.:

Synonyms:(R)-2-((S)-5-Bromo-2,3-dihydro-1H-indol-2-yl)-1-methoxy-4-phenyl-butan-2-ol

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Chemical Property of (R)-2-((S)-5-Bromo-2,3-dihydro-1H-indol-2-yl)-1-methoxy-4-phenyl-butan-2-ol

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Technology Process of (R)-2-((S)-5-Bromo-2,3-dihydro-1H-indol-2-yl)-1-methoxy-4-phenyl-butan-2-ol

There total 7 articles about (R)-2-((S)-5-Bromo-2,3-dihydro-1H-indol-2-yl)-1-methoxy-4-phenyl-butan-2-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: 96.0%

: 500548-75-4
tert-butyl (2S)-5-bromo-2-[(1R)-1-hydroxy-1-(methoxymethyl)-3-phenylpropyl]indoline-1-carboxylate

: 849480-33-7
(R)-2-((S)-5-Bromo-2,3-dihydro-1H-indol-2-yl)-1-methoxy-4-phenyl-butan-2-ol

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 3h;
DOI:10.1016/j.tet.2004.12.041

Reference yield:

: 79815-20-6,78348-24-0
(S)-indoline-2-carboxylic acid

: 849480-33-7
(R)-2-((S)-5-Bromo-2,3-dihydro-1H-indol-2-yl)-1-methoxy-4-phenyl-butan-2-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: sulfuric acid / 6 h / 80 °C

2.1: 31.4 g / CH₂Cl₂ / 20 °C

3.1: 93 percent / NBS / dimethylformamide / 2 h / 0 °C

4.1: 83 percent / i-propylmagnesium chloride / tetrahydrofuran / 0.5 h / -10 °C

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

5.2: 61 percent / tetrahydrofuran; hexane / 0.25 h / -78 °C

6.1: 68 percent / tetrahydrofuran / 0.25 h / -78 °C

7.1: 96 percent / TFA / CH₂Cl₂ / 3 h / 20 °C

With N-Bromosuccinimide; n-butyllithium; sulfuric acid; isopropylmagnesium chloride; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 6.1: Grignard addition;
DOI:10.1016/j.tet.2004.12.041

Reference yield:

: 141410-06-2
(S)-indoline-2-carboxylic acid methyl ester

: 849480-33-7
(R)-2-((S)-5-Bromo-2,3-dihydro-1H-indol-2-yl)-1-methoxy-4-phenyl-butan-2-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 31.4 g / CH₂Cl₂ / 20 °C

2.1: 93 percent / NBS / dimethylformamide / 2 h / 0 °C

3.1: 83 percent / i-propylmagnesium chloride / tetrahydrofuran / 0.5 h / -10 °C

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

4.2: 61 percent / tetrahydrofuran; hexane / 0.25 h / -78 °C

5.1: 68 percent / tetrahydrofuran / 0.25 h / -78 °C

6.1: 96 percent / TFA / CH₂Cl₂ / 3 h / 20 °C

With N-Bromosuccinimide; n-butyllithium; isopropylmagnesium chloride; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 5.1: Grignard addition;
DOI:10.1016/j.tet.2004.12.041