(2'S,5'S,3S)-6-methoxy-2-oxo-2'-phenyl-1'-[1-(3,3,3-trichloroethoxycarbonyl)-pyrrolidine-2S-carbonyl]-1,2-dihydrospiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid methyl ester

Base Information

• Chemical Name: (2'S,5'S,3S)-6-methoxy-2-oxo-2'-phenyl-1'-[1-(3,3,3-trichloroethoxycarbonyl)-pyrrolidine-2S-carbonyl]-1,2-dihydrospiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid methyl ester
• CAS No.: 1318074-92-8
• Molecular Formula: C₂₈H₂₈Cl₃N₃O₇
• Molecular Weight: 624.905

Synonyms:(2'S,5'S,3S)-6-methoxy-2-oxo-2'-phenyl-1'-[1-(3,3,3-trichloroethoxycarbonyl)-pyrrolidine-2S-carbonyl]-1,2-dihydrospiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid methyl ester

Chemical Property of (2'S,5'S,3S)-6-methoxy-2-oxo-2'-phenyl-1'-[1-(3,3,3-trichloroethoxycarbonyl)-pyrrolidine-2S-carbonyl]-1,2-dihydrospiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (2'S,5'S,3S)-6-methoxy-2-oxo-2'-phenyl-1'-[1-(3,3,3-trichloroethoxycarbonyl)-pyrrolidine-2S-carbonyl]-1,2-dihydrospiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid methyl ester

There total 15 articles about (2'S,5'S,3S)-6-methoxy-2-oxo-2'-phenyl-1'-[1-(3,3,3-trichloroethoxycarbonyl)-pyrrolidine-2S-carbonyl]-1,2-dihydrospiro[indole-3,3'-pyrrolidine]-5'-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: 50.0%

rac-(2'S,5'S,3S)-6-methoxy-2-oxo-2'-phenyl-1,2-dihydro-spiro[indole-3,3'-pyrrolodine]-5'-carboxylic acid methyl ester + N-2,2,2-trichloroethoxycarbonyl-L-prolinyl chloride (127940-23-2,107454-63-7) → (2'S,5'S,3S)-6-methoxy-2-oxo-2'-phenyl-1'-[1-(3,3,3-trichloroethoxycarbonyl)-pyrrolidine-2S-carbonyl]-1,2-dihydrospiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid methyl ester (1318074-92-8) + (2'R,5'R,3R)-6-methoxy-2-oxo-2'-phenyl-1'-[1-(3,3,3-trichloroethoxycarbonyl)-pyrrolidine-2S-carbonyl]-1,2-dihydrospiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid methyl ester (1318074-93-9)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 12h; Inert atmosphere; Resolution of racemate;

DOI:10.1039/c1ob05710c

Reference yield:

6-methoxy-3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-1-(2,4-dimethoxybenzyl)-1,3-dihydroindol-2-one (1318074-51-9) → (2'S,5'S,3S)-6-methoxy-2-oxo-2'-phenyl-1'-[1-(3,3,3-trichloroethoxycarbonyl)-pyrrolidine-2S-carbonyl]-1,2-dihydrospiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid methyl ester (1318074-92-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: methoxybenzene; trifluoroacetic acid / dichloromethane / 48 h / 50 °C / Inert atmosphere

2.1: potassium carbonate / N,N-dimethyl-formamide / 0.75 h / 20 °C / Inert atmosphere

3.1: samarium diiodide / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere

3.2: 80 °C / Inert atmosphere; Sealed tube

4.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 48 h / 20 °C / Inert atmosphere

5.1: lead(IV) tetraacetate / ethyl acetate / 0.25 h / 20 °C / Inert atmosphere

6.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / water; acetonitrile; tert-butyl alcohol / 2 h / 20 °C / Inert atmosphere

7.1: methanol; hexane / 2 h / 20 °C / Inert atmosphere

8.1: hydrogenchloride; hydrogen; palladium(II) hydroxide / methanol; water / 0.08 h / 760.05 Torr / Inert atmosphere

9.1: triethylamine / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere; Resolution of racemate

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; osmium(VIII) oxide; samarium diiodide; 2-methyl-but-2-ene; hydrogen; lead(IV) tetraacetate; palladium(II) hydroxide; potassium carbonate; methoxybenzene; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol;

DOI:10.1039/c1ob05710c

Reference yield:

6-methoxy-3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-1,3-dihydroindol-2-one (1318074-58-6) → (2'S,5'S,3S)-6-methoxy-2-oxo-2'-phenyl-1'-[1-(3,3,3-trichloroethoxycarbonyl)-pyrrolidine-2S-carbonyl]-1,2-dihydrospiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid methyl ester (1318074-92-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 0.75 h / 20 °C / Inert atmosphere

2.1: samarium diiodide / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere

2.2: 80 °C / Inert atmosphere; Sealed tube

3.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 48 h / 20 °C / Inert atmosphere

4.1: lead(IV) tetraacetate / ethyl acetate / 0.25 h / 20 °C / Inert atmosphere

5.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / water; acetonitrile; tert-butyl alcohol / 2 h / 20 °C / Inert atmosphere

6.1: methanol; hexane / 2 h / 20 °C / Inert atmosphere

7.1: hydrogenchloride; hydrogen; palladium(II) hydroxide / methanol; water / 0.08 h / 760.05 Torr / Inert atmosphere

8.1: triethylamine / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere; Resolution of racemate

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; osmium(VIII) oxide; samarium diiodide; 2-methyl-but-2-ene; hydrogen; lead(IV) tetraacetate; palladium(II) hydroxide; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol;

DOI:10.1039/c1ob05710c

upstream raw materials:

6-methoxy-3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-1-(2,4-dimethoxybenzyl)-1,3-dihydroindol-2-one

6-methoxy-3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-1,3-dihydroindol-2-one

3-(4-chlorobut-2-enyl)-3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-6-methoxy-1,3-dihydroindol-2-one

N-2,2,2-trichloroethoxycarbonyl-L-prolinyl chloride

Downstream raw materials:

(2S,3S,5aS,10aS)-6'-methoxy-3-phenyl-5a,6,7,8-tetrahydro-1H-spiro[dipyrrolo[1,2-a:1'2'-d]pyrazine-2,3'-indoline]-2',5,10(3H,10aH)-trione

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