6-(tert-butyldimethylsilanyloxy)-1-(3-phenylallyl)-(2S,3,3aR,6S,7,7aR)-hexahydro-1H-indole-2-carboxylic acid methyl ester

Base Information

• Chemical Name: 6-(tert-butyldimethylsilanyloxy)-1-(3-phenylallyl)-(2S,3,3aR,6S,7,7aR)-hexahydro-1H-indole-2-carboxylic acid methyl ester
• CAS No.: 486421-49-2
• Molecular Formula: C₂₅H₃₇NO₃Si
• Molecular Weight: 427.659

Synonyms:6-(tert-butyldimethylsilanyloxy)-1-(3-phenylallyl)-(2S,3,3aR,6S,7,7aR)-hexahydro-1H-indole-2-carboxylic acid methyl ester

Chemical Property of 6-(tert-butyldimethylsilanyloxy)-1-(3-phenylallyl)-(2S,3,3aR,6S,7,7aR)-hexahydro-1H-indole-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-(tert-butyldimethylsilanyloxy)-1-(3-phenylallyl)-(2S,3,3aR,6S,7,7aR)-hexahydro-1H-indole-2-carboxylic acid methyl ester

There total 9 articles about 6-(tert-butyldimethylsilanyloxy)-1-(3-phenylallyl)-(2S,3,3aR,6S,7,7aR)-hexahydro-1H-indole-2-carboxylic acid methyl ester 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%

Cinnamyl bromide (4392-24-9) + 6-(tert-butyldimethylsilanyloxy)-(2S,3,3aR,6S,7,7aR)-hexahydroindole-2-carboxylic acid methyl ester (486421-48-1) → 6-(tert-butyldimethylsilanyloxy)-1-(3-phenylallyl)-(2S,3,3aR,6S,7,7aR)-hexahydro-1H-indole-2-carboxylic acid methyl ester (486421-49-2)

Guidance literature:

With potassium carbonate; In toluene; at 60 ℃; for 15h;

DOI:10.1021/ja044280k

Reference yield:

(2S,3aR,7aR)-3a-hydroxy-6-oxo-2,3,3a,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (144534-49-6) → 6-(tert-butyldimethylsilanyloxy)-1-(3-phenylallyl)-(2S,3,3aR,6S,7,7aR)-hexahydro-1H-indole-2-carboxylic acid methyl ester (486421-49-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 26 g / dimethylaminopyridine; pyridine / CH₂Cl₂ / 20 h / Heating

2: 97 percent / cerium(III) chloride heptahydrate; NaBH₄ / tetrahydrofuran; methanol / 15 h / 0 °C

3: 93 percent / Pd₂(dba)3*CHCl₃; tribenzylphosphine; triethylamine / formic acid / tetrahydrofuran / 16 h / Heating

4: 97 percent / imidazole; dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 °C

5: 90 percent / triethylsilane; palladium(II) acetate; triethylamine / CH₂Cl₂ / 15 h / 20 °C

6: 96 percent / K₂CO₃ / toluene / 15 h / 60 °C

With pyridine; 1H-imidazole; triethylsilane; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; cerium(III) chloride; palladium diacetate; potassium carbonate; triethylamine; tribenzylphosphine; formic acid; In tetrahydrofuran; methanol; dichloromethane; toluene; 2: Luche reduction;

DOI:10.1021/ja044280k

Reference yield:

<2S-(2β,3aβ,7aβ)>-2,3,3a,6,7,7a-hexahydro-3a-benzoyloxy-6-oxo-1H-indole-1,2-dicarboxylic acid 1-benzyl 2-methyl ester (171523-63-0) → 6-(tert-butyldimethylsilanyloxy)-1-(3-phenylallyl)-(2S,3,3aR,6S,7,7aR)-hexahydro-1H-indole-2-carboxylic acid methyl ester (486421-49-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 97 percent / cerium(III) chloride heptahydrate; NaBH₄ / tetrahydrofuran; methanol / 15 h / 0 °C

2: 93 percent / Pd₂(dba)3*CHCl₃; tribenzylphosphine; triethylamine / formic acid / tetrahydrofuran / 16 h / Heating

3: 97 percent / imidazole; dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 °C

4: 90 percent / triethylsilane; palladium(II) acetate; triethylamine / CH₂Cl₂ / 15 h / 20 °C

5: 96 percent / K₂CO₃ / toluene / 15 h / 60 °C

With 1H-imidazole; triethylsilane; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; cerium(III) chloride; palladium diacetate; potassium carbonate; triethylamine; tribenzylphosphine; formic acid; In tetrahydrofuran; methanol; dichloromethane; toluene; 1: Luche reduction;

DOI:10.1021/ja044280k

upstream raw materials:

Cinnamyl bromide

6-(tert-butyldimethylsilanyloxy)-(2S,3,3aR,6S,7,7aR)-hexahydroindole-2-carboxylic acid methyl ester

tert-butyldimethylsilyl chloride

(2S,3aR,6S,7aR)-6-hydroxy-2,3,3a,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Downstream raw materials:

7-allyl-6-(tert-butyldimethylsilanyloxy)-1-(3-phenylallyl)-(2S,3,3aR,6S,7S,7aR)-hexahydro-1H-indole-2-carboxylic acid methyl ester

7-allyl-4-dimethylcarbamoylmethyl-1-(3-phenylallyl)-(2S,3,3aR,4R,7S,7aR)-hexahydro-1H-indole-2-carboxylic acid methoxymethylamide

7-allyl-6-(tert-butyldimethylsilanyloxy)-1-(3-phenylallyl)-(2S,3,3aR,6S,7S,7aR)-hexahydro-1H-indole-2-carboxylic acid methoxymethyl amide

2-[7-allyl-2-((4S)-methyl-5-oxotetrahydrofuran-2-yl)-1-(3-phenylallyl)-(2S,3,3aR,4R,7S,7aR)-hexahydro-1H-indol-4-yl]-N,N-dimethylacetamide

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