(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

Base Information

• Chemical Name: (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
• CAS No.: 912807-36-4
• Molecular Formula: C₃₂H₃₈F₇NO₃
• Molecular Weight: 617.647
• Mol file: 912807-36-4.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 13 articles about (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 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:

(1R,2R,3S)-2-(4-fluorophenyl)-3-hydroxycyclopentane-1-carboxylic acid (190269-78-4) → (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 (912807-36-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: HCl / 1 h / Heating

2.1: HBF₄ / 1,2-dichloro-ethane; heptane / -15 - 15 °C

2.2: KOH / methanol; H₂O / 3.5 h / 25 - 35 °C

2.3: 54 percent / heptane / 0.5 h / 70 °C

3.1: BH₃*THF / toluene / 3 h / 65 °C

4.1: i-Pr₂NEt; Ms₂O / toluene / 1.25 h / 38 °C

4.2: iPr₂NEt / toluene / 16 h / Heating

With hydrogenchloride; tetrafluoroboric acid; borane-THF; N-ethyl-N,N-diisopropylamine; Methanesulfonic anhydride; In n-heptane; 1,2-dichloro-ethane; toluene;

DOI:10.1021/jo061268x

Reference yield:

methyl (1R,2R,3S)-2-(4-fluorophenyl)-3-hydroxycyclopentane-1-carboxylate (190269-75-1) → (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 (912807-36-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: HBF₄ / 1,2-dichloro-ethane; heptane / -15 - 15 °C

1.2: KOH / methanol; H₂O / 3.5 h / 25 - 35 °C

1.3: 54 percent / heptane / 0.5 h / 70 °C

2.1: BH₃*THF / toluene / 3 h / 65 °C

3.1: i-Pr₂NEt; Ms₂O / toluene / 1.25 h / 38 °C

3.2: iPr₂NEt / toluene / 16 h / Heating

With tetrafluoroboric acid; borane-THF; N-ethyl-N,N-diisopropylamine; Methanesulfonic anhydride; In n-heptane; 1,2-dichloro-ethane; toluene;

DOI:10.1021/jo061268x

Reference yield:

(R)-piperidine-1,3-dicarboxylic acid 1-benzyl ester 3-tert-butyl ester (912807-34-2) → (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 (912807-36-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 90 percent / H₂ / Pd/C / ethanol; ethyl acetate / 8 h / 1034.3 Torr

2.1: i-Pr₂NEt; Ms₂O / toluene / 1.25 h / 38 °C

2.2: iPr₂NEt / toluene / 16 h / Heating

With hydrogen; N-ethyl-N,N-diisopropylamine; Methanesulfonic anhydride; palladium on activated charcoal; In ethanol; ethyl acetate; toluene;

DOI:10.1021/jo061268x

upstream raw materials:

(R)-3-N-tert-butoxycarbonylaminopiperidine

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

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

(R)-piperidine-1,3-dicarboxylic acid 1-benzyl ester 3-tert-butyl ester