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

Base Information

Chemical Name: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
CAS No.:828921-44-4
Molecular Formula:C₂₉H₃₈N₂O₃
Molecular Weight:462.632
Hs Code.:

Synonyms: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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Chemical Property of 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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Technology Process of 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

There total 15 articles about 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 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: 79.0%

: 18871-66-4
N,N-dimethylacetamide dimethyl acetal

: 828921-43-3
(5S)-[7-allyl-6-hydroxy-1-(3-phenylallyl)-(2S,3,3aR,6S,7S,7aR)-hexahydro-1H-indol-2-yl]-3-methyldihydrofuran-2-one

: 828921-44-4
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

Guidance literature:: In xylene; at 130 ℃; for 16h;
DOI:10.1021/ja044280k

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

: 828921-44-4
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

Guidance literature:: Multi-step reaction with 16 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: 91 percent / imidazole; dimethylaminopyridine / CH₂Cl₂ / 19 h / 20 °C

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

12.2: 97 percent / CH₂Cl₂; hexane / 19 h / 20 °C

13.1: naphthalene; lithium / tetrahydrofuran / 3 h / -78 °C

13.2: 76 percent / tetrahydrofuran / 0.08 h / -78 °C

14.1: 84 percent / L-Selectride / tetrahydrofuran / 16 h / -78 - 0 °C

15.1: 71 percent / p-toluenesufonic acid monohydrate / methanol / 20 h / 20 °C

16.1: 79 percent / xylene / 16 h / 130 °C

With pyridine; 1H-imidazole; triethylsilane; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; cerium(III) chloride; tetrapropylammonium perruthennate; naphthalene; tetrabutyl ammonium fluoride; palladium diacetate; dimethylaluminum chloride; lithium; potassium hexamethylsilazane; L-Selectride; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; tribenzylphosphine; formic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; xylene; 2.1: Luche reduction / 10.1: Luche reduction / 16.1: 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

: 828921-44-4
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

Guidance literature:: Multi-step reaction with 15 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: 91 percent / imidazole; dimethylaminopyridine / CH₂Cl₂ / 19 h / 20 °C

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

11.2: 97 percent / CH₂Cl₂; hexane / 19 h / 20 °C

12.1: naphthalene; lithium / tetrahydrofuran / 3 h / -78 °C

12.2: 76 percent / tetrahydrofuran / 0.08 h / -78 °C

13.1: 84 percent / L-Selectride / tetrahydrofuran / 16 h / -78 - 0 °C

14.1: 71 percent / p-toluenesufonic acid monohydrate / methanol / 20 h / 20 °C

15.1: 79 percent / xylene / 16 h / 130 °C

With 1H-imidazole; triethylsilane; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; cerium(III) chloride; tetrapropylammonium perruthennate; naphthalene; tetrabutyl ammonium fluoride; palladium diacetate; dimethylaluminum chloride; lithium; potassium hexamethylsilazane; L-Selectride; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; tribenzylphosphine; formic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; xylene; 1.1: Luche reduction / 9.1: Luche reduction / 15.1: Eschenmoser-Claisen rearrangement;
DOI:10.1021/ja044280k