(3S,5R)-3-Allyl-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-(2,4-difluoro-phenyl)-pyrrolidin-2-one

Base Information

• Chemical Name: (3S,5R)-3-Allyl-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-(2,4-difluoro-phenyl)-pyrrolidin-2-one
• CAS No.: 808189-18-6
• Molecular Formula: C₂₁H₃₁F₂NO₂Si
• Molecular Weight: 395.565

Synonyms:(3S,5R)-3-Allyl-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-(2,4-difluoro-phenyl)-pyrrolidin-2-one

Chemical Property of (3S,5R)-3-Allyl-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-(2,4-difluoro-phenyl)-pyrrolidin-2-one

Chemical Property:

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Technology Process of (3S,5R)-3-Allyl-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-(2,4-difluoro-phenyl)-pyrrolidin-2-one

There total 8 articles about (3S,5R)-3-Allyl-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-(2,4-difluoro-phenyl)-pyrrolidin-2-one 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: 70.0%

allyl bromide (106-95-6) + 1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-(2,4-difluoro-phenyl)-pyrrolidin-2-one (808189-11-9) → (3S,5R)-3-Allyl-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-(2,4-difluoro-phenyl)-pyrrolidin-2-one (808189-18-6)

Guidance literature:

1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-(2,4-difluoro-phenyl)-pyrrolidin-2-one; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

allyl bromide; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2004.09.001

Reference yield:

1,3-Difluorobenzene (372-18-9) → (3S,5R)-3-Allyl-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-(2,4-difluoro-phenyl)-pyrrolidin-2-one (808189-18-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 80 percent / aluminum chloride / 0 - 80 °C

2.1: 90 percent / aq. LiOH / tetrahydrofuran

3.1: 100 percent / toluene / 16 h / Heating

4.1: 80 percent / TiCl₄; Et₃SiH / CH₂Cl₂ / 16 h / -78 - 20 °C

5.1: 95 percent / SOCl₂ / tetrahydrofuran / 0 - 20 °C

6.1: 80 percent / NaOEt / ethanol / 45 °C

7.1: 85 percent / aq. HCl / tetrahydrofuran / Heating

8.1: 75 percent / KH / dimethylformamide / 1 h / 20 °C

9.1: LDA / tetrahydrofuran / -78 °C

9.2: 70 percent / tetrahydrofuran

With hydrogenchloride; triethylsilane; lithium hydroxide; aluminium trichloride; thionyl chloride; sodium ethanolate; titanium tetrachloride; potassium hydride; lithium diisopropyl amide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmcl.2004.09.001

Reference yield:

4-(2,4-difluorophenyl)-4-oxobutanoic acid (110931-77-6) → (3S,5R)-3-Allyl-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-(2,4-difluoro-phenyl)-pyrrolidin-2-one (808189-18-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 100 percent / toluene / 16 h / Heating

2.1: 80 percent / TiCl₄; Et₃SiH / CH₂Cl₂ / 16 h / -78 - 20 °C

3.1: 95 percent / SOCl₂ / tetrahydrofuran / 0 - 20 °C

4.1: 80 percent / NaOEt / ethanol / 45 °C

5.1: 85 percent / aq. HCl / tetrahydrofuran / Heating

6.1: 75 percent / KH / dimethylformamide / 1 h / 20 °C

7.1: LDA / tetrahydrofuran / -78 °C

7.2: 70 percent / tetrahydrofuran

With hydrogenchloride; triethylsilane; thionyl chloride; sodium ethanolate; titanium tetrachloride; potassium hydride; lithium diisopropyl amide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmcl.2004.09.001

upstream raw materials:

allyl bromide

1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-(2,4-difluoro-phenyl)-pyrrolidin-2-one

1,3-Difluorobenzene

4-(2,4-difluorophenyl)-4-oxobutanoic acid

Downstream raw materials:

2-[1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-(2,4-difluoro-phenyl)-2-oxo-pyrrolidin-3-yl]-N-(3-chloro-2-methyl-benzyl)-acetamide

[(3R,5R)-3-[(3-Chloro-2-methyl-benzylcarbamoyl)-methyl]-5-(2,4-difluoro-phenyl)-2-oxo-pyrrolidin-1-yl]-acetic acid

[(3R,5R)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-(2,4-difluoro-phenyl)-2-oxo-pyrrolidin-3-yl]-acetic acid

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