(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

Base Information

Chemical Name:(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
CAS No.:1318074-95-1
Molecular Formula:C₂₇H₂₉N₃O₄
Molecular Weight:459.545
Hs Code.:

Synonyms:(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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Chemical Property of (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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Technology Process of (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

There total 13 articles about (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 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: 93.0%

: 1318074-91-7
(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

: 1318074-95-1
(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

Guidance literature:: With ammonium chloride; zinc; In tetrahydrofuran; methanol; at 20 ℃; for 24h; Inert atmosphere;
DOI:10.1039/c1ob05710c

Reference yield:

: 847550-38-3
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

: 1318074-95-1
(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

Guidance literature:: Multi-step reaction with 9 steps

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

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

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

9.1: ammonium chloride; zinc / tetrahydrofuran; methanol / 24 h / 20 °C / Inert atmosphere

With hydrogenchloride; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; samarium diiodide; 2-methyl-but-2-ene; hydrogen; palladium(II) hydroxide; potassium carbonate; ammonium chloride; 4-methylmorpholine N-oxide; triethylamine; zinc; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol;
DOI:10.1039/c1ob05710c

Reference yield:

: 1130682-67-5
2-hydroxy-N-(3-methoxyphenyl)-N-propylacetamide

: 1318074-95-1
(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

Guidance literature:: Multi-step reaction with 11 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

11.1: ammonium chloride; zinc / tetrahydrofuran; methanol / 24 h / 20 °C / Inert atmosphere

With hydrogenchloride; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; samarium diiodide; 2-methyl-but-2-ene; hydrogen; palladium(II) hydroxide; potassium carbonate; ammonium chloride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; zinc; 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