1-Pyrrolidinecarboxamide, N-(3-chloro-4-cyano-2-methylphenyl)-3-[[(1,1-dimethylethyl)dimethylsilyl] oxy]-2-[(1S)-1-hydroxy-2-methylpropyl]-, (2R,3R)-

Base Information

Chemical Name:1-Pyrrolidinecarboxamide, N-(3-chloro-4-cyano-2-methylphenyl)-3-[[(1,1-dimethylethyl)dimethylsilyl] oxy]-2-[(1S)-1-hydroxy-2-methylpropyl]-, (2R,3R)-
CAS No.:757247-89-5
Molecular Formula:C23H36ClN3O3Si
Molecular Weight:466.096
Hs Code.:

1-Pyrrolidinecarboxamide,
N-(3-chloro-4-cyano-2-methylphenyl)-3-[[(1,1-dimethylethyl)dimethylsilyl]
oxy]-2-[(1S)-1-hydroxy-2-methylpropyl]-, (2R,3R)-

Synonyms:

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Chemical Property of 1-Pyrrolidinecarboxamide, N-(3-chloro-4-cyano-2-methylphenyl)-3-[[(1,1-dimethylethyl)dimethylsilyl] oxy]-2-[(1S)-1-hydroxy-2-methylpropyl]-, (2R,3R)-

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Technology Process of 1-Pyrrolidinecarboxamide, N-(3-chloro-4-cyano-2-methylphenyl)-3-[[(1,1-dimethylethyl)dimethylsilyl] oxy]-2-[(1S)-1-hydroxy-2-methylpropyl]-, (2R,3R)-

There total 15 articles about 1-Pyrrolidinecarboxamide, N-(3-chloro-4-cyano-2-methylphenyl)-3-[[(1,1-dimethylethyl)dimethylsilyl] oxy]-2-[(1S)-1-hydroxy-2-methylpropyl]-, (2R,3R)- 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:

: 496841-07-7
(2S,3R)-N-tert-Butyloxycarbonyl-3-benzoyloxy-2-pyrrolidinecarboxylic Acid Methyl Ester

: 757247-89-5
(2R,3R)-3-(tert-butyldimethylsilanyloxy)-N-(3-chloro-4-cyano-2-methylphenyl)-2-((S)-1-hydroxy-2-methylpropyl)pyrrolidine-1-carboxamide

Guidance literature:: Multi-step reaction with 7 steps

1: 72 percent / KOH / methanol / 2.42 h / 0 °C

2: i-Pr₂NEt / DMAP / CH₂Cl₂ / 48 h / 20 °C

3: LiBHEt₃ / tetrahydrofuran / -78 - 20 °C

4: 4-methylmorpholine N-oxide / n-Pr₄NRuO₄ / acetonitrile; CH₂Cl₂ / 4 h / 20 °C

5: CsF / 29 h / 20 - 50 °C

6: TFA / CH₂Cl₂ / 0.5 h / 20 °C

7: i-Pr₂NEt / CH₂Cl₂ / -78 - 20 °C

With potassium hydroxide; lithium triethylborohydride; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; cesium fluoride; trifluoroacetic acid; dmap; tetrapropylammonium perruthennate; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1021/jm070312d

Reference yield:

: 184046-77-3
(2S,3R)-N-tert-butyloxycarbonyl-3-(tert-butyldimethylsilyloxy)-2-pyrrolidinecarboxylic acid methyl ester

: 757247-89-5
(2R,3R)-3-(tert-butyldimethylsilanyloxy)-N-(3-chloro-4-cyano-2-methylphenyl)-2-((S)-1-hydroxy-2-methylpropyl)pyrrolidine-1-carboxamide

Guidance literature:: Multi-step reaction with 5 steps

1: LiBHEt₃ / tetrahydrofuran / -78 - 20 °C

2: 4-methylmorpholine N-oxide / n-Pr₄NRuO₄ / acetonitrile; CH₂Cl₂ / 4 h / 20 °C

3: CsF / 29 h / 20 - 50 °C

4: TFA / CH₂Cl₂ / 0.5 h / 20 °C

5: i-Pr₂NEt / CH₂Cl₂ / -78 - 20 °C

With lithium triethylborohydride; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; cesium fluoride; trifluoroacetic acid; tetrapropylammonium perruthennate; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/jm070312d

Reference yield:

: 130966-46-0
(2S,3R)-N-tert-Butyloxycarbonyl-3-hydroxy-2-pyrrolidinecarboxylic Acid Methyl Ester

: 757247-89-5
(2R,3R)-3-(tert-butyldimethylsilanyloxy)-N-(3-chloro-4-cyano-2-methylphenyl)-2-((S)-1-hydroxy-2-methylpropyl)pyrrolidine-1-carboxamide

Guidance literature:: Multi-step reaction with 6 steps

1: i-Pr₂NEt / DMAP / CH₂Cl₂ / 48 h / 20 °C

2: LiBHEt₃ / tetrahydrofuran / -78 - 20 °C

3: 4-methylmorpholine N-oxide / n-Pr₄NRuO₄ / acetonitrile; CH₂Cl₂ / 4 h / 20 °C

4: CsF / 29 h / 20 - 50 °C

5: TFA / CH₂Cl₂ / 0.5 h / 20 °C

6: i-Pr₂NEt / CH₂Cl₂ / -78 - 20 °C

With lithium triethylborohydride; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; cesium fluoride; trifluoroacetic acid; dmap; tetrapropylammonium perruthennate; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/jm070312d