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

Base Information

• Chemical Name: (1S,2R,3R)-3-(tert-butyldimethylsilanyloxymethyl)-2-(4-fluorophenyl)cyclopentanol
• CAS No.: 405512-97-2
• Molecular Formula: C₁₈H₂₉FO₂Si
• Molecular Weight: 324.511
• Mol file: 405512-97-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about (1S,2R,3R)-3-(tert-butyldimethylsilanyloxymethyl)-2-(4-fluorophenyl)cyclopentanol 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: 74.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (1S,2R,3R)-2-(4-fluorophenyl)-3-hydroxymethylcyclopentanol (405512-96-1) → (1S,2R,3R)-3-(tert-butyldimethylsilanyloxymethyl)-2-(4-fluorophenyl)cyclopentanol (405512-97-2)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 18h;

DOI:10.1021/jo061268x

Reference yield:

methyl (1R,2R,3S)-2-(4-fluorophenyl)-3-hydroxycyclopentane-1-carboxylate (190269-75-1) → (1S,2R,3R)-3-(tert-butyldimethylsilanyloxymethyl)-2-(4-fluorophenyl)cyclopentanol (405512-97-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / LiAlH₄ / tetrahydrofuran / 2 h / 20 °C

2: 74 percent / imidazole / dimethylformamide / 18 h / 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo061268x

Reference yield:

(1R,2R,3S)-2-(4-fluorophenyl)-3-hydroxycyclopentane-1-carboxylic acid (190269-78-4) → (1S,2R,3R)-3-(tert-butyldimethylsilanyloxymethyl)-2-(4-fluorophenyl)cyclopentanol (405512-97-2)

Guidance literature:

Multi-step reaction with 3 steps

1: HCl / 1 h / Heating

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

3: 74 percent / imidazole / dimethylformamide / 18 h / 20 °C

With 1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo061268x

upstream raw materials:

tert-butyldimethylsilyl chloride

(1S,2R,3R)-2-(4-fluorophenyl)-3-hydroxymethylcyclopentanol

(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:

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

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

(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

3,5-bis(trifluoromethyl)benzoic acid (1S,2R,3R)-3-(tert-butyldimethylsilanyloxymethyl)-2-(4-fluorophenyl)cyclopentyl