[(1R,2S,3S)-3-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-2-(4-fluoro-phenyl)-cyclopentyl]-methyl-amine

Base Information

• Chemical Name: [(1R,2S,3S)-3-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-2-(4-fluoro-phenyl)-cyclopentyl]-methyl-amine
• CAS No.: 190271-59-1
• Molecular Formula: C₂₂H₂₂F₇NO
• Molecular Weight: 449.412

Synonyms:[(1R,2S,3S)-3-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-2-(4-fluoro-phenyl)-cyclopentyl]-methyl-amine

Chemical Property of [(1R,2S,3S)-3-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-2-(4-fluoro-phenyl)-cyclopentyl]-methyl-amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1R,2S,3S)-3-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-2-(4-fluoro-phenyl)-cyclopentyl]-methyl-amine

There total 14 articles about [(1R,2S,3S)-3-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-2-(4-fluoro-phenyl)-cyclopentyl]-methyl-amine 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,2S,3R)-2-(4-Fluoro-phenyl)-3-hydroxy-cyclopentanecarboxylic acid methyl ester → [(1R,2S,3S)-3-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-2-(4-fluoro-phenyl)-cyclopentyl]-methyl-amine (190271-59-1)

Guidance literature:

Multi-step reaction with 10 steps

1: NaOH / methanol

2: HCl

3: HBF₄

4: 98 percent / NaOH / methanol / 60 °C

5: oxalyl chloride; DMF / CH₂Cl₂

6: aq. NaN₃ / acetone / -10 °C

7: toluene / 80 °C

8: DIPEA; DMAP / toluene / 100 °C

9: NaH / dimethylformamide

10: H₂ / Pd/C / ethanol

With hydrogenchloride; dmap; sodium hydroxide; tetrafluoroboric acid; sodium azide; oxalyl dichloride; hydrogen; sodium hydride; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; palladium on activated charcoal; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 7: Curtius rearrangement;

DOI:10.1016/j.bmcl.2006.06.044

Reference yield:

(+/-)-trans-3-oxo-2-(4-fluorophenyl)cyclopentane carboxylic acid methyl ester → [(1R,2S,3S)-3-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-2-(4-fluoro-phenyl)-cyclopentyl]-methyl-amine (190271-59-1)

Guidance literature:

Multi-step reaction with 11 steps

1: 77 percent / NaBH₄ / methanol

2: NaOH / methanol

3: HCl

4: HBF₄

5: 98 percent / NaOH / methanol / 60 °C

6: oxalyl chloride; DMF / CH₂Cl₂

7: aq. NaN₃ / acetone / -10 °C

8: toluene / 80 °C

9: DIPEA; DMAP / toluene / 100 °C

10: NaH / dimethylformamide

11: H₂ / Pd/C / ethanol

With hydrogenchloride; dmap; sodium hydroxide; sodium tetrahydroborate; tetrafluoroboric acid; sodium azide; oxalyl dichloride; hydrogen; sodium hydride; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; palladium on activated charcoal; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 8: Curtius rearrangement;

DOI:10.1016/j.bmcl.2006.06.044

Reference yield:

(1R,2R,3S)-2-(4-fluorophenyl)-3-hydroxycyclopentane-1-carboxylic acid (190269-78-4) → [(1R,2S,3S)-3-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-2-(4-fluoro-phenyl)-cyclopentyl]-methyl-amine (190271-59-1)

Guidance literature:

Multi-step reaction with 9 steps

1: HCl

2: HBF₄

3: 98 percent / NaOH / methanol / 60 °C

4: oxalyl chloride; DMF / CH₂Cl₂

5: aq. NaN₃ / acetone / -10 °C

6: toluene / 80 °C

7: DIPEA; DMAP / toluene / 100 °C

8: NaH / dimethylformamide

9: H₂ / Pd/C / ethanol

With hydrogenchloride; dmap; sodium hydroxide; tetrafluoroboric acid; sodium azide; oxalyl dichloride; hydrogen; sodium hydride; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; palladium on activated charcoal; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 6: Curtius rearrangement;

DOI:10.1016/j.bmcl.2006.06.044

upstream raw materials:

[(1R,2S,3S)-3-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-2-(4-fluoro-phenyl)-cyclopentyl]-methyl-carbamic acid benzyl ester

(1S)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl-2,2,2-trichloroethanimidoate

(1R,2R,3S)-3[(R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy]-2-(4-fluorophenyl)cyclopentane-1-carboxylic acid methyl ester

((1R),(2R),(3S))-3-((1R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy)-2-(4-fluorophenyl)cyclopentane-carboxylic acid

Downstream raw materials:

{[(1R,2S,3S)-3-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-2-(4-fluoro-phenyl)-cyclopentyl]-methyl-amino}-acetic acid tert-butyl ester

{[(1R,2S,3S)-3-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-2-(4-fluoro-phenyl)-cyclopentyl]-methyl-amino}-acetic acid

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