(2'R,5'R,3R)-6-methoxy-2-oxo-2'-phenyl-1-propyl-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'R,5'R,3R)-6-methoxy-2-oxo-2'-phenyl-1-propyl-1'-[1-(3,3,3-trichloroethoxycarbonyl)-pyrrolidine-2S-carbonyl]-1,2-dihydrospiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid methyl ester
• CAS No.: 1318074-91-7
• Molecular Formula: C₃₁H₃₄Cl₃N₃O₇
• Molecular Weight: 666.986

Synonyms:(2'R,5'R,3R)-6-methoxy-2-oxo-2'-phenyl-1-propyl-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'R,5'R,3R)-6-methoxy-2-oxo-2'-phenyl-1-propyl-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:

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

There total 12 articles about (2'R,5'R,3R)-6-methoxy-2-oxo-2'-phenyl-1-propyl-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-propyl-1,2-dihydrospiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid methyl ester + N-2,2,2-trichloroethoxycarbonyl-L-prolinyl chloride (127940-23-2,107454-63-7) → (2'R,5'R,3R)-6-methoxy-2-oxo-2'-phenyl-1-propyl-1'-[1-(3,3,3-trichloroethoxycarbonyl)-pyrrolidine-2S-carbonyl]-1,2-dihydrospiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid methyl ester (1318074-91-7) + (2'S,5'S,3S)-6-methoxy-2-oxo-2'-phenyl-1-propyl-1'-[1-(3,3,3-trichloroethoxycarbonyl)-pyrrolidine-2S-carbonyl]-1,2-dihydrospiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid methyl ester (1318074-90-6)

Guidance literature:

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

DOI:10.1039/c1ob05710c

Reference yield:

N-(3-methoxyphenyl)-2-oxo-N-propylacetamide → (2'R,5'R,3R)-6-methoxy-2-oxo-2'-phenyl-1-propyl-1'-[1-(3,3,3-trichloroethoxycarbonyl)-pyrrolidine-2S-carbonyl]-1,2-dihydrospiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid methyl ester (1318074-91-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: dichloromethane / 1 h / 20 °C / Inert atmosphere

1.2: 16 h / 20 °C / Inert atmosphere

2.1: potassium carbonate / N,N-dimethyl-formamide / 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 / 60 h / 20 °C / Inert atmosphere

5.1: sodium periodate / tetrahydrofuran / 2 h / Inert atmosphere; Reflux

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 periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; samarium diiodide; 2-methyl-but-2-ene; hydrogen; palladium(II) hydroxide; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; 1.1: Pummerer type reaction / 1.2: Pummerer type reaction;

DOI:10.1039/c1ob05710c

Reference yield:

2-hydroxy-N-(3-methoxyphenyl)-N-propylacetamide (1130682-67-5) → (2'R,5'R,3R)-6-methoxy-2-oxo-2'-phenyl-1-propyl-1'-[1-(3,3,3-trichloroethoxycarbonyl)-pyrrolidine-2S-carbonyl]-1,2-dihydrospiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid methyl ester (1318074-91-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: dimethyl sulfoxide / dichloromethane / 0.25 h / -78 °C

1.2: 0.5 h / -78 °C / Inert atmosphere

1.3: 3 h / -78 - 20 °C / Inert atmosphere

2.1: dichloromethane / 1 h / 20 °C / Inert atmosphere

2.2: 16 h / 20 °C / Inert atmosphere

3.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

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

4.2: 80 °C / Inert atmosphere; Sealed tube

5.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 60 h / 20 °C / Inert atmosphere

6.1: sodium periodate / tetrahydrofuran / 2 h / Inert atmosphere; Reflux

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

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

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

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

With hydrogenchloride; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; samarium diiodide; 2-methyl-but-2-ene; hydrogen; palladium(II) hydroxide; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; 1.1: Swern oxidation / 1.2: Swern oxidation / 2.1: Pummerer type reaction / 2.2: Pummerer type reaction;

DOI:10.1039/c1ob05710c

upstream raw materials:

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

2-hydroxy-N-(3-methoxyphenyl)-N-propylacetamide

2-acetoxy-N-(3-methoxyphenyl)-N-propylacetamide

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-propyl-1,3-dihydroindol-2-one

Downstream raw materials:

(2R,3R,5aS,10aR)-6'-methoxy-3-phenyl-1'-propyl-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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