[(1R,2R,3S)-3-{1-(3,5-bis(trifluoromethyl)phenyl)vinyloxy}-2-(4-fluorophenyl)cyclopentylmethoxy]tert-butyldimethylsilane

Base Information

• Chemical Name: [(1R,2R,3S)-3-{1-(3,5-bis(trifluoromethyl)phenyl)vinyloxy}-2-(4-fluorophenyl)cyclopentylmethoxy]tert-butyldimethylsilane
• CAS No.: 405512-99-4
• Molecular Formula: C₂₈H₃₃F₇O₂Si
• Molecular Weight: 562.643
• Mol file: 405512-99-4.mol

Synonyms:[(1R,2R,3S)-3-{1-(3,5-bis(trifluoromethyl)phenyl)vinyloxy}-2-(4-fluorophenyl)cyclopentylmethoxy]tert-butyldimethylsilane

Chemical Property of [(1R,2R,3S)-3-{1-(3,5-bis(trifluoromethyl)phenyl)vinyloxy}-2-(4-fluorophenyl)cyclopentylmethoxy]tert-butyldimethylsilane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1R,2R,3S)-3-{1-(3,5-bis(trifluoromethyl)phenyl)vinyloxy}-2-(4-fluorophenyl)cyclopentylmethoxy]tert-butyldimethylsilane

There total 5 articles about [(1R,2R,3S)-3-{1-(3,5-bis(trifluoromethyl)phenyl)vinyloxy}-2-(4-fluorophenyl)cyclopentylmethoxy]tert-butyldimethylsilane 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:

(1S,2R,3R)-3-(tert-butyldimethylsilanyloxymethyl)-2-(4-fluorophenyl)cyclopentanol (405512-97-2) → [(1R,2R,3S)-3-{1-(3,5-bis(trifluoromethyl)phenyl)vinyloxy}-2-(4-fluorophenyl)cyclopentylmethoxy]tert-butyldimethylsilane (405512-99-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

2.1: Cp₂TiMe₂ / toluene / 1 h / 0 °C

2.2: 486 mg / toluene / 4 h / 80 °C

With triethylamine; dimethyltitanocene; In dichloromethane; toluene;

DOI:10.1021/jo061268x

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → [(1R,2R,3S)-3-{1-(3,5-bis(trifluoromethyl)phenyl)vinyloxy}-2-(4-fluorophenyl)cyclopentylmethoxy]tert-butyldimethylsilane (405512-99-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 74 percent / imidazole / dimethylformamide / 18 h / 20 °C

2.1: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

3.1: Cp₂TiMe₂ / toluene / 1 h / 0 °C

3.2: 486 mg / toluene / 4 h / 80 °C

With 1H-imidazole; triethylamine; dimethyltitanocene; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo061268x

Reference yield:

methyl (1R,2R,3S)-2-(4-fluorophenyl)-3-hydroxycyclopentane-1-carboxylate (190269-75-1) → [(1R,2R,3S)-3-{1-(3,5-bis(trifluoromethyl)phenyl)vinyloxy}-2-(4-fluorophenyl)cyclopentylmethoxy]tert-butyldimethylsilane (405512-99-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 100 percent / LiAlH₄ / tetrahydrofuran / 2 h / 20 °C

2.1: 74 percent / imidazole / dimethylformamide / 18 h / 20 °C

3.1: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

4.1: Cp₂TiMe₂ / toluene / 1 h / 0 °C

4.2: 486 mg / toluene / 4 h / 80 °C

With 1H-imidazole; lithium aluminium tetrahydride; triethylamine; dimethyltitanocene; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo061268x

upstream raw materials:

(1S,2R,3R)-3-(tert-butyldimethylsilanyloxymethyl)-2-(4-fluorophenyl)cyclopentanol

tert-butyldimethylsilyl chloride

(1R,2R,3S)-2-(4-fluorophenyl)-3-hydroxycyclopentane-1-carboxylic acid

methyl (1R,2R,3S)-2-(4-fluorophenyl)-3-hydroxycyclopentane-1-carboxylate

Downstream raw materials:

(R)-1-[(1R,2R,3S)-3-{(R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy}-2-(4-fluorophenyl)cyclopentylmethyl]piperidine-3-carboxylic acid tert-butyl ester

[(1R,2R,3S)-3-{(R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy}-2-(4-fluorophenyl)cyclopentyl]methanol