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

Base Information

Chemical Name:7-allyl-4-dimethylcarbamoylmethyl-1-(3-phenylallyl)-(2S,3,3aR,4R,7S,7aR)-hexahydro-1H-indole-2-carboxylic acid methoxymethylamide
CAS No.:828921-39-7
Molecular Formula:C₂₇H₃₇N₃O₃
Molecular Weight:451.609
Hs Code.:

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

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

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

There total 10 articles about 7-allyl-4-dimethylcarbamoylmethyl-1-(3-phenylallyl)-(2S,3,3aR,4R,7S,7aR)-hexahydro-1H-indole-2-carboxylic acid methoxymethylamide 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:

: 144534-49-6
(2S,3aR,7aR)-3a-hydroxy-6-oxo-2,3,3a,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

: 828921-39-7
7-allyl-4-dimethylcarbamoylmethyl-1-(3-phenylallyl)-(2S,3,3aR,4R,7S,7aR)-hexahydro-1H-indole-2-carboxylic acid methoxymethylamide

Guidance literature:: Multi-step reaction with 12 steps

1.1: 26 g / dimethylaminopyridine; pyridine / CH₂Cl₂ / 20 h / Heating

2.1: 97 percent / cerium(III) chloride heptahydrate; NaBH₄ / tetrahydrofuran; methanol / 15 h / 0 °C

3.1: 93 percent / Pd₂(dba)3*CHCl₃; tribenzylphosphine; triethylamine / formic acid / tetrahydrofuran / 16 h / Heating

4.1: 97 percent / imidazole; dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 °C

5.1: 90 percent / triethylsilane; palladium(II) acetate; triethylamine / CH₂Cl₂ / 15 h / 20 °C

6.1: 96 percent / K₂CO₃ / toluene / 15 h / 60 °C

7.1: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

8.1: 88 percent / 4-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 15 h / 20 °C

9.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran / 0.08 h / -90 °C

9.2: 66 percent / tetrahydrofuran / 0.5 h / -90 °C

10.1: 87 percent / cerium(III) chloride heptahydrate; sodium borohydride / tetrahydrofuran; methanol / 1.5 h / 20 °C

11.1: 98 percent / xylene / 19 h / 130 °C

12.1: dimethylaluminum chloride / CH₂Cl₂; hexane / 1 h / 20 °C

12.2: 77 percent / CH₂Cl₂; hexane / 20 h / 20 °C

With pyridine; 1H-imidazole; triethylsilane; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; cerium(III) chloride; tetrapropylammonium perruthennate; tetrabutyl ammonium fluoride; palladium diacetate; dimethylaluminum chloride; potassium hexamethylsilazane; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; tribenzylphosphine; formic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; xylene; 2.1: Luche reduction / 10.1: Luche reduction / 11.1: Eschenmoser-Claisen rearrangement;
DOI:10.1021/ja044280k

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

: 828921-39-7
7-allyl-4-dimethylcarbamoylmethyl-1-(3-phenylallyl)-(2S,3,3aR,4R,7S,7aR)-hexahydro-1H-indole-2-carboxylic acid methoxymethylamide

Guidance literature:: Multi-step reaction with 11 steps

1.1: 97 percent / cerium(III) chloride heptahydrate; NaBH₄ / tetrahydrofuran; methanol / 15 h / 0 °C

2.1: 93 percent / Pd₂(dba)3*CHCl₃; tribenzylphosphine; triethylamine / formic acid / tetrahydrofuran / 16 h / Heating

3.1: 97 percent / imidazole; dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 °C

4.1: 90 percent / triethylsilane; palladium(II) acetate; triethylamine / CH₂Cl₂ / 15 h / 20 °C

5.1: 96 percent / K₂CO₃ / toluene / 15 h / 60 °C

6.1: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

7.1: 88 percent / 4-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 15 h / 20 °C

8.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran / 0.08 h / -90 °C

8.2: 66 percent / tetrahydrofuran / 0.5 h / -90 °C

9.1: 87 percent / cerium(III) chloride heptahydrate; sodium borohydride / tetrahydrofuran; methanol / 1.5 h / 20 °C

10.1: 98 percent / xylene / 19 h / 130 °C

11.1: dimethylaluminum chloride / CH₂Cl₂; hexane / 1 h / 20 °C

11.2: 77 percent / CH₂Cl₂; hexane / 20 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; dimethylaluminum chloride; potassium hexamethylsilazane; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; tribenzylphosphine; formic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; xylene; 1.1: Luche reduction / 9.1: Luche reduction / 10.1: Eschenmoser-Claisen rearrangement;
DOI:10.1021/ja044280k

Reference yield:

: 171523-45-8
(2S,3aR,6S,7aR)-3a-(benzoyloxy)-6-hydroxy-2,3,3a,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

: 828921-39-7
7-allyl-4-dimethylcarbamoylmethyl-1-(3-phenylallyl)-(2S,3,3aR,4R,7S,7aR)-hexahydro-1H-indole-2-carboxylic acid methoxymethylamide

Guidance literature:: Multi-step reaction with 10 steps

1.1: 93 percent / Pd₂(dba)3*CHCl₃; tribenzylphosphine; triethylamine / formic acid / tetrahydrofuran / 16 h / Heating

2.1: 97 percent / imidazole; dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 °C

3.1: 90 percent / triethylsilane; palladium(II) acetate; triethylamine / CH₂Cl₂ / 15 h / 20 °C

4.1: 96 percent / K₂CO₃ / toluene / 15 h / 60 °C

5.1: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

6.1: 88 percent / 4-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 15 h / 20 °C

7.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran / 0.08 h / -90 °C

7.2: 66 percent / tetrahydrofuran / 0.5 h / -90 °C

8.1: 87 percent / cerium(III) chloride heptahydrate; sodium borohydride / tetrahydrofuran; methanol / 1.5 h / 20 °C

9.1: 98 percent / xylene / 19 h / 130 °C

10.1: dimethylaluminum chloride / CH₂Cl₂; hexane / 1 h / 20 °C

10.2: 77 percent / CH₂Cl₂; hexane / 20 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; dimethylaluminum chloride; potassium hexamethylsilazane; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; tribenzylphosphine; formic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; xylene; 8.1: Luche reduction / 9.1: Eschenmoser-Claisen rearrangement;
DOI:10.1021/ja044280k