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

Base Information

Chemical Name:tert-butyl (2S)-5-bromo-2-[(1R)-1-hydroxy-1-(methoxymethyl)-3-phenylpropyl]indoline-1-carboxylate
CAS No.:500548-75-4
Molecular Formula:C₂₄H₃₀BrNO₄
Molecular Weight:476.411
Hs Code.:

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

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Chemical Property of tert-butyl (2S)-5-bromo-2-[(1R)-1-hydroxy-1-(methoxymethyl)-3-phenylpropyl]indoline-1-carboxylate

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Technology Process of tert-butyl (2S)-5-bromo-2-[(1R)-1-hydroxy-1-(methoxymethyl)-3-phenylpropyl]indoline-1-carboxylate

There total 7 articles about tert-butyl (2S)-5-bromo-2-[(1R)-1-hydroxy-1-(methoxymethyl)-3-phenylpropyl]indoline-1-carboxylate 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: 68.0%

: 90878-19-6
phenethylmagnesium chloride

: 500548-54-9
tert-butyl (2S)-5-bromo-2-(methoxyacetyl)indoline-1-carboxylate

: (S)-5-Bromo-2-((S)-1-hydroxy-1-methoxymethyl-3-phenyl-propyl)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

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

Guidance literature:: In tetrahydrofuran; at -78 ℃; for 0.25h;
DOI:10.1016/j.tet.2004.12.041

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 5 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

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

Reference yield:

: 500548-52-7
1-tert-butyl 2-methyl (2S)-5-bromoindoline-1,2-dicarboxylate

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

Guidance literature:: Multi-step reaction with 3 steps

1.1: 83 percent / i-propylmagnesium chloride / tetrahydrofuran / 0.5 h / -10 °C

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

2.2: 61 percent / tetrahydrofuran; hexane / 0.25 h / -78 °C

3.1: 68 percent / tetrahydrofuran / 0.25 h / -78 °C

With n-butyllithium; isopropylmagnesium chloride; In tetrahydrofuran; hexane; 3.1: Grignard addition;
DOI:10.1016/j.tet.2004.12.041