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

Base Information

Chemical Name:1-(3-phenylallyl)-6-oxo-(2S,3,3aR,6,7,7aR)-hexahydro-1H-indole-2-carboxylic acid methyl ester
CAS No.:486421-65-2
Molecular Formula:C₁₉H₂₁NO₃
Molecular Weight:311.381
Hs Code.:

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

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

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

There total 9 articles about 1-(3-phenylallyl)-6-oxo-(2S,3,3aR,6,7,7aR)-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: 88.0%

: 486421-50-5
1-(3-phenylallyl)-6-hydroxy-(2S,3,3aR,6S,7,7aR)-hexahydro-1H-indole-2-carboxylic acid methyl ester

: 486421-65-2
1-(3-phenylallyl)-6-oxo-(2S,3,3aR,6,7,7aR)-hexahydro-1H-indole-2-carboxylic acid methyl ester

Guidance literature:: With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; In dichloromethane; at 20 ℃; for 15h;
DOI:10.1021/ja044280k

Reference yield: 88.0%

: 486421-49-2
6-(tert-butyldimethylsilanyloxy)-1-(3-phenylallyl)-(2S,3,3aR,6S,7,7aR)-hexahydro-1H-indole-2-carboxylic acid methyl ester

: 486421-65-2
1-(3-phenylallyl)-6-oxo-(2S,3,3aR,6,7,7aR)-hexahydro-1H-indole-2-carboxylic acid methyl ester

Guidance literature:: With N-methyl-2-indolinone; tetrapropylammonium perruthennate; In dichloromethane;
DOI:10.1021/ja028603t

Reference yield:

: 171523-63-0
<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

: 486421-65-2
1-(3-phenylallyl)-6-oxo-(2S,3,3aR,6,7,7aR)-hexahydro-1H-indole-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 7 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

6: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

7: 88 percent / 4-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 15 h / 20 °C

With 1H-imidazole; triethylsilane; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; cerium(III) chloride; tetrapropylammonium perruthennate; tetrabutyl ammonium fluoride; palladium diacetate; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; tribenzylphosphine; formic acid; In tetrahydrofuran; methanol; dichloromethane; toluene; 1: Luche reduction;
DOI:10.1021/ja044280k