[4-[3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-phenyl)-propyl]-2-(4-fluoro-phenyl)-3,4-dihydro-2H-pyrazol-3-yl]-methanol

Base Information

• Chemical Name: [4-[3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-phenyl)-propyl]-2-(4-fluoro-phenyl)-3,4-dihydro-2H-pyrazol-3-yl]-methanol
• CAS No.: 869588-41-0
• Molecular Formula: C₂₅H₃₄F₂N₂O₂Si
• Molecular Weight: 460.639

Synonyms:[4-[3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-phenyl)-propyl]-2-(4-fluoro-phenyl)-3,4-dihydro-2H-pyrazol-3-yl]-methanol

Chemical Property of [4-[3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-phenyl)-propyl]-2-(4-fluoro-phenyl)-3,4-dihydro-2H-pyrazol-3-yl]-methanol

Chemical Property:

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Technology Process of [4-[3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-phenyl)-propyl]-2-(4-fluoro-phenyl)-3,4-dihydro-2H-pyrazol-3-yl]-methanol

There total 9 articles about [4-[3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-phenyl)-propyl]-2-(4-fluoro-phenyl)-3,4-dihydro-2H-pyrazol-3-yl]-methanol 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: 76.0%

[(3S,4R)-4-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(4-fluoro-phenyl)-propyl]-2-(4-fluoro-phenyl)-3,4-dihydro-2H-pyrazol-3-yl]-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-methanone (869588-33-0) → [4-[3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-phenyl)-propyl]-2-(4-fluoro-phenyl)-3,4-dihydro-2H-pyrazol-3-yl]-methanol (869588-41-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -78 ℃; for 4.5h;

DOI:10.1039/b510100j

Reference yield:

4-benzyloxy-1-(4-fluorophenyl)but-2-yn-1-ol (869588-29-4) → [4-[3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-phenyl)-propyl]-2-(4-fluoro-phenyl)-3,4-dihydro-2H-pyrazol-3-yl]-methanol (869588-41-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: imidazole / dimethylformamide / 3.5 h

2.1: Na₂CO₃; H₂ / Pd/C / ethanol / 19 h

3.1: 3.643 g / H₂ / Pd/C / ethanol / 2.25 h

4.1: 80 percent / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

5.1: 71 percent / DBU; LiCl / acetonitrile / 2.5 h / 20 °C

6.1: toluene; hexane / 64 h / 20 °C

6.2: 84 percent / TFA / CH₂Cl₂ / 0.33 h

7.1: Mg; I₂ / diethyl ether / 1.33 h

7.2: BiCl₃ / diethyl ether / 4 h / Heating

7.3: 320.8 mg / Cu(OAc)2; Et₃N / CH₂Cl₂ / 12.5 h / 20 °C

8.1: 76 percent / LiAlH₄ / tetrahydrofuran / 4.5 h / -78 °C

With 1H-imidazole; lithium aluminium tetrahydride; hydrogen; iodine; sodium carbonate; Dess-Martin periodane; magnesium; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 4.1: Dess-Martin oxidation / 5.1: Horner-Wadsworth-Emmons olefination;

DOI:10.1039/b510100j

Reference yield:

[4-benzyloxy-1-(4-fluoro-phenyl)-butoxy]-tert-butyl-dimethyl-silane → [4-[3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-phenyl)-propyl]-2-(4-fluoro-phenyl)-3,4-dihydro-2H-pyrazol-3-yl]-methanol (869588-41-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 3.643 g / H₂ / Pd/C / ethanol / 2.25 h

2.1: 80 percent / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

3.1: 71 percent / DBU; LiCl / acetonitrile / 2.5 h / 20 °C

4.1: toluene; hexane / 64 h / 20 °C

4.2: 84 percent / TFA / CH₂Cl₂ / 0.33 h

5.1: Mg; I₂ / diethyl ether / 1.33 h

5.2: BiCl₃ / diethyl ether / 4 h / Heating

5.3: 320.8 mg / Cu(OAc)2; Et₃N / CH₂Cl₂ / 12.5 h / 20 °C

6.1: 76 percent / LiAlH₄ / tetrahydrofuran / 4.5 h / -78 °C

With lithium aluminium tetrahydride; hydrogen; iodine; Dess-Martin periodane; magnesium; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; toluene; acetonitrile; 2.1: Dess-Martin oxidation / 3.1: Horner-Wadsworth-Emmons olefination;

DOI:10.1039/b510100j

upstream raw materials:

[(3S,4R)-4-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(4-fluoro-phenyl)-propyl]-2-(4-fluoro-phenyl)-3,4-dihydro-2H-pyrazol-3-yl]-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-methanone

4-(tert-butyl-dimethyl-silanyloxy)-4-(4-fluoro-phenyl)-butyraldehyde

4-benzyloxy-1-(4-fluorophenyl)but-2-yn-1-ol

4-(tert-butyldimethylsilanyloxy)-4-(4-fluorophenyl)butan-1-ol

Downstream raw materials:

toluene-4-sulfonic acid 4-[3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-phenyl)-propyl]-2-(4-fluoro-phenyl)-3,4-dihydro-2H-pyrazol-3-ylmethyl ester

4-[4-[3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-phenyl)-propyl]-2-(4-fluoro-phenyl)-3,4-dihydro-2H-pyrazol-3-ylmethoxy]-phenol

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