1-[(R)-4-(5-benzyloxy-1-methylindol-3-yl)-1-(tert-butyldimethylsilyloxy)-2-butyl]imidazole-4-carboxamide

Base Information

Chemical Name:1-[(R)-4-(5-benzyloxy-1-methylindol-3-yl)-1-(tert-butyldimethylsilyloxy)-2-butyl]imidazole-4-carboxamide
CAS No.:294862-78-5
Molecular Formula:C₃₀H₄₀N₄O₃Si
Molecular Weight:532.758
Hs Code.:

Synonyms:1-[(R)-4-(5-benzyloxy-1-methylindol-3-yl)-1-(tert-butyldimethylsilyloxy)-2-butyl]imidazole-4-carboxamide

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Chemical Property of 1-[(R)-4-(5-benzyloxy-1-methylindol-3-yl)-1-(tert-butyldimethylsilyloxy)-2-butyl]imidazole-4-carboxamide

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Technology Process of 1-[(R)-4-(5-benzyloxy-1-methylindol-3-yl)-1-(tert-butyldimethylsilyloxy)-2-butyl]imidazole-4-carboxamide

There total 9 articles about 1-[(R)-4-(5-benzyloxy-1-methylindol-3-yl)-1-(tert-butyldimethylsilyloxy)-2-butyl]imidazole-4-carboxamide 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:

: 58630-07-2
5-(benzyloxy)-1-methyl-1H-indole-3-carbaldehyde

: 294862-78-5
1-[(R)-4-(5-benzyloxy-1-methylindol-3-yl)-1-(tert-butyldimethylsilyloxy)-2-butyl]imidazole-4-carboxamide

Guidance literature:: Multi-step reaction with 8 steps

1.1: 86.3 percent / NaH / dimethylformamide / 20 °C

2.1: 90 percent / H₂ / Pd/C / ethanol; tetrahydrofuran / 1.5 h / 20 °C / 1520 Torr

3.1: 77 percent / DIBAL-H / CH₂Cl₂; hexane / 0.5 h / -78 °C

4.1: n-BuLi / tetrahydrofuran / 2 h / -78 - 20 °C

4.2: 87.7 percent / tetrahydrofuran / 2 h / 20 °C

5.1: 53.5 percent / AD-mix-α; water / 2-methyl-propan-2-ol / 4 h / 0 °C

6.1: 84.5 percent / imidazole / dimethylformamide / 0 - 20 °C

7.1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

8.1: NaH / dimethylformamide / 1 h / 70 °C

8.2: 3.10 g / dimethylformamide / 24 h / 70 °C

With 1H-imidazole; AD-mix-α; n-butyllithium; water; hydrogen; sodium hydride; diisobutylaluminium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Wittig-Horner reaction / 4.2: Wittig reaction / 5.1: Sharpless asymmetric hydroxylation;
DOI:10.1021/jm0306374

Reference yield:

: 742105-16-4
ethyl 3-(5-benzyloxy-1-methylindol-3-yl)acrylate

: 294862-78-5
1-[(R)-4-(5-benzyloxy-1-methylindol-3-yl)-1-(tert-butyldimethylsilyloxy)-2-butyl]imidazole-4-carboxamide

Guidance literature:: Multi-step reaction with 7 steps

1.1: 90 percent / H₂ / Pd/C / ethanol; tetrahydrofuran / 1.5 h / 20 °C / 1520 Torr

2.1: 77 percent / DIBAL-H / CH₂Cl₂; hexane / 0.5 h / -78 °C

3.1: n-BuLi / tetrahydrofuran / 2 h / -78 - 20 °C

3.2: 87.7 percent / tetrahydrofuran / 2 h / 20 °C

4.1: 53.5 percent / AD-mix-α; water / 2-methyl-propan-2-ol / 4 h / 0 °C

5.1: 84.5 percent / imidazole / dimethylformamide / 0 - 20 °C

6.1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

7.1: NaH / dimethylformamide / 1 h / 70 °C

7.2: 3.10 g / dimethylformamide / 24 h / 70 °C

With 1H-imidazole; AD-mix-α; n-butyllithium; water; hydrogen; sodium hydride; diisobutylaluminium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 3.2: Wittig reaction / 4.1: Sharpless asymmetric hydroxylation;
DOI:10.1021/jm0306374

Reference yield:

: 26832-08-6
imidazole-4-carboxamide

: (S)-4-(5-benzyloxy-1-methylindol-3-yl)-1-(tert-butyldimethylsilyloxy)butan-2-ol mesylate

: 294862-78-5
1-[(R)-4-(5-benzyloxy-1-methylindol-3-yl)-1-(tert-butyldimethylsilyloxy)-2-butyl]imidazole-4-carboxamide

Guidance literature:: imidazole-4-carboxamide; With sodium hydride; In N,N-dimethyl-formamide; at 70 ℃; for 1h;

(S)-4-(5-benzyloxy-1-methylindol-3-yl)-1-(tert-butyldimethylsilyloxy)butan-2-ol mesylate; In N,N-dimethyl-formamide; at 70 ℃; for 24h;
DOI:10.1021/jm0306374