4-(2-(pyrrolidin-1-yl)-4-(trifluoromethyl)benzyl)piperazine-1-carboxylic acid 1,1,1,3,3,3-hexafluoropropan-2-yl ester

Base Information

• Chemical Name: 4-(2-(pyrrolidin-1-yl)-4-(trifluoromethyl)benzyl)piperazine-1-carboxylic acid 1,1,1,3,3,3-hexafluoropropan-2-yl ester
• CAS No.: 1446817-84-0
• Molecular Formula: C₂₀H₂₂F₉N₃O₂
• Molecular Weight: 507.399

Synonyms:4-(2-(pyrrolidin-1-yl)-4-(trifluoromethyl)benzyl)piperazine-1-carboxylic acid 1,1,1,3,3,3-hexafluoropropan-2-yl ester

Chemical Property of 4-(2-(pyrrolidin-1-yl)-4-(trifluoromethyl)benzyl)piperazine-1-carboxylic acid 1,1,1,3,3,3-hexafluoropropan-2-yl ester

Chemical Property:

Purity/Quality:

99%, ^*data from raw suppliers

ABX-1431 >98% ^*data from reagent suppliers

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Useful:

• Description: ABX-1431 (1446817-84-0) is a potent (IC50 = 14 nM in vitro, 2.2 nM in human PC3 cells) and very selective (>100-fold over hABHD6, >200-fold over hPLA2G7) inhibitor of monoacylglycerol lipase (MAGL).1 Active in a rat formalin pain test at 3mg/kg. Orally bioavailable and CNS penetrant.

Technology Process of 4-(2-(pyrrolidin-1-yl)-4-(trifluoromethyl)benzyl)piperazine-1-carboxylic acid 1,1,1,3,3,3-hexafluoropropan-2-yl ester

There total 8 articles about 4-(2-(pyrrolidin-1-yl)-4-(trifluoromethyl)benzyl)piperazine-1-carboxylic acid 1,1,1,3,3,3-hexafluoropropan-2-yl 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: 92.0%

2-(pyrrolidin-1-yl)-4-(trifluoromethyl)benzaldehyde (1374603-97-0) + 1,1,1,3,3,3-hexafluoropropan-2-yl piperazine-1-carboxylate, 2,2,2-trifluoroacetate salt → 4-(2-(pyrrolidin-1-yl)-4-(trifluoromethyl)benzyl)piperazine-1-carboxylic acid 1,1,1,3,3,3-hexafluoropropan-2-yl ester (1446817-84-0)

Guidance literature:

1,1,1,3,3,3-hexafluoropropan-2-yl piperazine-1-carboxylate, 2,2,2-trifluoroacetate salt; With triethylamine; In ethyl acetate; at 20 - 25 ℃; for 1.25h; Large scale;

2-(pyrrolidin-1-yl)-4-(trifluoromethyl)benzaldehyde; In ethyl acetate; at 20 - 25 ℃; for 3.25h; Inert atmosphere; Large scale;

With sodium tris(acetoxy)borohydride; In ethyl acetate; at 20 - 25 ℃; Inert atmosphere; Large scale;

Reference yield: 92.0%

2-(pyrrolidin-1-yl)-4-(trifluoromethyl)benzaldehyde (1374603-97-0) + 1,1,1,3,3,3-hexafluoropropan-2-yl piperazine-1-carboxylate hydrochloride → 4-(2-(pyrrolidin-1-yl)-4-(trifluoromethyl)benzyl)piperazine-1-carboxylic acid 1,1,1,3,3,3-hexafluoropropan-2-yl ester (1446817-84-0)

Guidance literature:

1,1,1,3,3,3-hexafluoropropan-2-yl piperazine-1-carboxylate hydrochloride; With triethylamine; In ethyl acetate; at 20 - 25 ℃; for 1.25h; Large scale;

2-(pyrrolidin-1-yl)-4-(trifluoromethyl)benzaldehyde; In ethyl acetate; at 20 - 25 ℃; for 3h; Inert atmosphere; Large scale;

With sodium tris(acetoxy)borohydride; In ethyl acetate; at 20 - 25 ℃; for 15.5h; Inert atmosphere; Large scale;

Reference yield: 79.0%

bis(trichloromethyl) carbonate (32315-10-9) + 1,1,1,3',3',3'-hexafluoro-propanol (920-66-1) + 1-[[2-(pyrrolidin-1-yl)-4-(trifluoromethyl)phenyl]methyl]piperazine (1446819-17-5) → 4-(2-(pyrrolidin-1-yl)-4-(trifluoromethyl)benzyl)piperazine-1-carboxylic acid 1,1,1,3,3,3-hexafluoropropan-2-yl ester (1446817-84-0)

Guidance literature:

bis(trichloromethyl) carbonate; 1,1,1,3',3',3'-hexafluoro-propanol; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

1-[[2-(pyrrolidin-1-yl)-4-(trifluoromethyl)phenyl]methyl]piperazine; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.8b00951

upstream raw materials:

2-Fluoro-4-(trifluoromethyl)benzaldehyde

2-(pyrrolidin-1-yl)-4-(trifluoromethyl)benzaldehyde

tert-butyl 4-[[2-(pyrrolidin-1-yl)-4-(trifluoromethyl)phenyl]methyl]piperazine-1-carboxylate

bis(trichloromethyl) carbonate

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