tert-butyl 4-methyl-4-((S)-3-methyl-4-((S)-1-(4-(trifluoromethyl)phenyl)ethyl)piperazin-1-yl)piperidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl 4-methyl-4-((S)-3-methyl-4-((S)-1-(4-(trifluoromethyl)phenyl)ethyl)piperazin-1-yl)piperidine-1-carboxylate
• CAS No.: 306297-00-7
• Molecular Formula: C₂₅H₃₈F₃N₃O₂
• Molecular Weight: 469.591
• Mol file: 306297-00-7.mol

Synonyms:tert-butyl 4-methyl-4-((S)-3-methyl-4-((S)-1-(4-(trifluoromethyl)phenyl)ethyl)piperazin-1-yl)piperidine-1-carboxylate

Chemical Property of tert-butyl 4-methyl-4-((S)-3-methyl-4-((S)-1-(4-(trifluoromethyl)phenyl)ethyl)piperazin-1-yl)piperidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 4-methyl-4-((S)-3-methyl-4-((S)-1-(4-(trifluoromethyl)phenyl)ethyl)piperazin-1-yl)piperidine-1-carboxylate

There total 10 articles about tert-butyl 4-methyl-4-((S)-3-methyl-4-((S)-1-(4-(trifluoromethyl)phenyl)ethyl)piperazin-1-yl)piperidine-1-carboxylate 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: 88.0%

methylmagnesium bromide (75-16-1) + 4-Cyano-4-{(S)-3-methyl-4-[(S)-1-(4-trifluoromethyl-phenyl)-ethyl]-piperazin-1-yl}-piperidine-1-carboxylic acid tert-butyl ester (306296-99-1) → tert-butyl 4-methyl-4-((S)-3-methyl-4-((S)-1-(4-(trifluoromethyl)phenyl)ethyl)piperazin-1-yl)piperidine-1-carboxylate (306297-00-7)

Guidance literature:

In tetrahydrofuran; diethyl ether; at 0 - 20 ℃; for 19h;

Reference yield: 25.4%

tert-butyl-4-methyl-4-[(3S)-3-methylpiperazin-1-yl]piperidine-1-carboxylate (306296-78-6) + 1-(4-trifluoromethylphenyl)ethanone (709-63-7) → 4-methyl-4-[(3S)-3-methyl-4-[(1R)-1-[4-(trifluoromethyl)phenyl]ethyl]-1-piperazinyl]-1-piperidinecarboxylic acid 1,1-dimethylethyl ester + tert-butyl 4-methyl-4-((S)-3-methyl-4-((S)-1-(4-(trifluoromethyl)phenyl)ethyl)piperazin-1-yl)piperidine-1-carboxylate (306297-00-7)

Guidance literature:

tert-butyl-4-methyl-4-[(3S)-3-methylpiperazin-1-yl]piperidine-1-carboxylate; With triethylamine; In 1,2-dichloro-ethane; at 20 ℃; for 0.5h;

1-(4-trifluoromethylphenyl)ethanone; With sodium tris(acetoxy)borohydride; acetic acid; In 1,2-dichloro-ethane; at 20 ℃; for 22h; Further stages.;

DOI:10.1039/b707175b

Reference yield:

1-(4-trifluoromethylphenyl)ethanone (709-63-7) → tert-butyl 4-methyl-4-((S)-3-methyl-4-((S)-1-(4-(trifluoromethyl)phenyl)ethyl)piperazin-1-yl)piperidine-1-carboxylate (306297-00-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 84 percent / 2M borane-methyl sulfide complex / (S)-2-methyl oxaborolidine / tetrahydrofuran / 0.25 h / cooling

2: 96 percent / Et₃N / CH₂Cl₂ / 1 h / cooling

3: 1.5 g / 2,2,6,6-tetramethylpiperidine / acetonitrile / 16 h / Heating

4: TFA / basification

5: 2.16 g / Ti(OiPr)4 / CH₂Cl₂; toluene / 44 h / 20 °C

6: 1.85 g / tetrahydrofuran; diethyl ether / 19 h / 20 °C / cooling

With 2,2,6,6-tetramethyl-piperidine; titanium(IV) isopropylate; dimethylsulfide borane complex; triethylamine; trifluoroacetic acid; 2-methyl oxaborolidine; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; acetonitrile; 3: Sn2 displacement;

DOI:10.1021/jm0155401

upstream raw materials:

methylmagnesium bromide

4-Cyano-4-{(S)-3-methyl-4-[(S)-1-(4-trifluoromethyl-phenyl)-ethyl]-piperazin-1-yl}-piperidine-1-carboxylic acid tert-butyl ester

tert-butyl-4-methyl-4-[(3S)-3-methylpiperazin-1-yl]piperidine-1-carboxylate

1-(4-trifluoromethylphenyl)ethanone

Downstream raw materials:

2-methyl-4-(4-methylpiperidin-4-yl)-1-[1-(4-trifluoromethylphenyl)ethyl]piperazine

Sch 350634

Sch 350581