rac-(6S,7R,8S,8aR)-8-(3-chloro-2-fluoro-phenyl)-7-(4-chloro-2-fluoro-phenyl)-2-((S)-3,4-dihydroxy-butyl)-6-(2,2-dimethyl-propyl)-1-oxo-octahydro-pyrrolo[1,2-a]pyrazine-7-carbonitrile

Base Information

Chemical Name:rac-(6S,7R,8S,8aR)-8-(3-chloro-2-fluoro-phenyl)-7-(4-chloro-2-fluoro-phenyl)-2-((S)-3,4-dihydroxy-butyl)-6-(2,2-dimethyl-propyl)-1-oxo-octahydro-pyrrolo[1,2-a]pyrazine-7-carbonitrile
CAS No.:1364614-53-8
Molecular Formula:C₂₉H₃₃Cl₂F₂N₃O₃
Molecular Weight:580.502
Hs Code.:

rac-(6S,7R,8S,8aR)-8-(3-chloro-2-fluoro-phenyl)-7-(4-chloro-2-fluoro-phenyl)-2-((S)-3,4-dihydroxy-butyl)-6-(2,2-dimethyl-propyl)-1-oxo-octahydro-pyrrolo[1,2-a]pyrazine-7-carbonitrile

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Chemical Property of rac-(6S,7R,8S,8aR)-8-(3-chloro-2-fluoro-phenyl)-7-(4-chloro-2-fluoro-phenyl)-2-((S)-3,4-dihydroxy-butyl)-6-(2,2-dimethyl-propyl)-1-oxo-octahydro-pyrrolo[1,2-a]pyrazine-7-carbonitrile

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Technology Process of rac-(6S,7R,8S,8aR)-8-(3-chloro-2-fluoro-phenyl)-7-(4-chloro-2-fluoro-phenyl)-2-((S)-3,4-dihydroxy-butyl)-6-(2,2-dimethyl-propyl)-1-oxo-octahydro-pyrrolo[1,2-a]pyrazine-7-carbonitrile

There total 12 articles about rac-(6S,7R,8S,8aR)-8-(3-chloro-2-fluoro-phenyl)-7-(4-chloro-2-fluoro-phenyl)-2-((S)-3,4-dihydroxy-butyl)-6-(2,2-dimethyl-propyl)-1-oxo-octahydro-pyrrolo[1,2-a]pyrazine-7-carbonitrile 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: 46.0%

: rac-(6S,7R,8S,8aR)-8-(3-chloro-2-fluorophenyl)-7-(4-chloro-2-fluorophenyl)-2-((S)-3,4-dihydroxybutyl)-6-(2,2-dimethylpropyl)-1-oxo-octahydropyrrolo[1,2-a]pyrazine-7-carbonitrile

: 1364614-53-8
rac-(6S,7R,8S,8aR)-8-(3-chloro-2-fluoro-phenyl)-7-(4-chloro-2-fluoro-phenyl)-2-((S)-3,4-dihydroxy-butyl)-6-(2,2-dimethyl-propyl)-1-oxo-octahydro-pyrrolo[1,2-a]pyrazine-7-carbonitrile

: 1364616-38-5
(6R,7S,8R,8aS)-8-(3-chloro-2-fluorophenyl)-7-(4-chloro-2-fluorophenyl)-2-((S)-3,4-dihydroxybutyl)-6-(2,2-dimethylpropyl)-1-oxo-octahydropyrrolo[1,2-a]pyrazine-7-carbonitrile

Guidance literature:: With chiral SFC chromatography; Purification / work up; Resolution of diastereomers;

Reference yield:

: 926-36-3
4,4-dimethylpentanal

: 1364614-53-8
rac-(6S,7R,8S,8aR)-8-(3-chloro-2-fluoro-phenyl)-7-(4-chloro-2-fluoro-phenyl)-2-((S)-3,4-dihydroxy-butyl)-6-(2,2-dimethyl-propyl)-1-oxo-octahydro-pyrrolo[1,2-a]pyrazine-7-carbonitrile

: 1364616-38-5
(6R,7S,8R,8aS)-8-(3-chloro-2-fluorophenyl)-7-(4-chloro-2-fluorophenyl)-2-((S)-3,4-dihydroxybutyl)-6-(2,2-dimethylpropyl)-1-oxo-octahydropyrrolo[1,2-a]pyrazine-7-carbonitrile

Guidance literature:: Multi-step reaction with 10 steps

1.1: dichloromethane / 20 °C

2.1: triethylamine; silver fluoride / dichloromethane / 18 h / 20 °C

2.2: 2 h / 100 °C

3.1: sodium tris(acetoxy)borohydride / dichloromethane / 48 h / 20 °C

4.1: dichloromethane / 18 h / 20 °C

5.1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 18 h / 20 °C

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 - 20 °C

7.1: triethylamine / dichloromethane / 1 h / 0 °C

8.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C

9.1: hydrogenchloride; water / tetrahydrofuran / 2 h / 20 °C

10.1: chiral SFC chromatography / Resolution of diastereomers

With hydrogenchloride; tetrabutyl ammonium fluoride; water; silver fluoride; sodium tris(acetoxy)borohydride; caesium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

: 1219086-88-0
racemic (2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-( 4-chloro-2-fluorophenyl)-4-cyano-5-(2,2-dimethylpropyl)pyrrolidine-2-carboxylic acid tert-butyl ester

: 1364614-53-8
rac-(6S,7R,8S,8aR)-8-(3-chloro-2-fluoro-phenyl)-7-(4-chloro-2-fluoro-phenyl)-2-((S)-3,4-dihydroxy-butyl)-6-(2,2-dimethyl-propyl)-1-oxo-octahydro-pyrrolo[1,2-a]pyrazine-7-carbonitrile

: 1364616-38-5
(6R,7S,8R,8aS)-8-(3-chloro-2-fluorophenyl)-7-(4-chloro-2-fluorophenyl)-2-((S)-3,4-dihydroxybutyl)-6-(2,2-dimethylpropyl)-1-oxo-octahydropyrrolo[1,2-a]pyrazine-7-carbonitrile

Guidance literature:: Multi-step reaction with 8 steps

1: sodium tris(acetoxy)borohydride / dichloromethane / 48 h / 20 °C

2: dichloromethane / 18 h / 20 °C

3: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 18 h / 20 °C

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 - 20 °C

5: triethylamine / dichloromethane / 1 h / 0 °C

6: caesium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C

7: hydrogenchloride; water / tetrahydrofuran / 2 h / 20 °C

8: chiral SFC chromatography / Resolution of diastereomers

With hydrogenchloride; tetrabutyl ammonium fluoride; water; sodium tris(acetoxy)borohydride; caesium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;