4-N-BOC-CYCLOHEXYACETIC ACID METHYL ESTER

Base Information

• Chemical Name: 4-N-BOC-CYCLOHEXYACETIC ACID METHYL ESTER
• CAS No.: 215789-45-0
• Molecular Formula: C14H25 N O4
• Molecular Weight: 271.357
• Mol file: 215789-45-0.mol

Synonyms:trans-2-[4-[(N-tert-Butoxycarbonyl)amino]cyclohexyl]aceticacid methyl ester; trans-2-[4-[(tert-Butoxycarbonyl)amino]cyclohexyl]aceticacid methyl ester

Chemical Property of 4-N-BOC-CYCLOHEXYACETIC ACID METHYL ESTER

Chemical Property:

• Vapor Pressure: 1.82E-05mmHg at 25°C
• Refractive Index: 1.474
• Boiling Point: 363.3°Cat760mmHg
• PKA: 12.42±0.40(Predicted)
• Flash Point: 173.5°C
• Density: 1.05g/cm³

Purity/Quality:

98%min ^*data from raw suppliers

trans-2-[4-[(tert-Butoxycarbonyl)amino]cyclohexyl]aceticAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

Useful:

• Uses: trans-2-[4-[(tert-Butoxycarbonyl)amino]cyclohexyl]acetic Acid Methyl Ester, is an intermediate for the synthesis of Cariprazine (C183490), a novel antipsychotic acting on dopamine D3/D2 receptors.

Technology Process of 4-N-BOC-CYCLOHEXYACETIC ACID METHYL ESTER

There total 6 articles about 4-N-BOC-CYCLOHEXYACETIC ACID METHYL 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: 57.0%

methyl 2-{4-[(N-(tert-butoxycarbonyl))amino]cyclohexylidene}acetate → trans-2-(1-(4-(N-tert-butoxycarbonyl)amino)cyclohexyl)acetic acid methyl ester (215789-45-0)

Guidance literature:

With palladium on activated charcoal; hydrogen; In tetrahydrofuran; at 20 ℃; for 10h; under 750.075 Torr; Inert atmosphere;

Reference yield:

methanol (67-56-1) + t-butyl [trans-4-(2-diazoacetyl)cyclohexyl]carbamate (609805-49-4) → trans-2-(1-(4-(N-tert-butoxycarbonyl)amino)cyclohexyl)acetic acid methyl ester (215789-45-0)

Guidance literature:

With silver benzoate; triethylamine; at -25 - 20 ℃; for 3h;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + trans-4-aminocyclohexylacetic acid methyl ester (76308-27-5) → trans-2-(1-(4-(N-tert-butoxycarbonyl)amino)cyclohexyl)acetic acid methyl ester (215789-45-0)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 18h;

DOI:10.1021/jm000090i

upstream raw materials:

di-tert-butyl dicarbonate

trans-4-aminocyclohexylacetic acid methyl ester

trans-(4-amino)-cyclohexylacetic acid hydrogen sulfate

methanol

Downstream raw materials:

trans-4-aminocyclohexylacetic acid methyl ester hydrochloride

trans-2-(4-tert-butoxycarbonylamino-cyclohexyl)-3-hydroxy-3-(6-methoxy-[1,5]naphthyridin-4-yl)-propionic acid methyl ester

Cariprazine

trans N-tert-butoxycarbonyl-4-{2-[4-(2,3-dichlorophenyl)-piperazin-1-yl]ethyl}-cyclohexylamine

Refernces

• 1、 -. "4-(1-AMINO-ETHYL)-CYCLOHEXYLAMINE DERIVATIVES". Page/Page column 28. . Retrieved 2010/03/02.
• 2、 Stemp, Geoffrey,Ashmeade, Tracey,Branch, Clive L.,Hadley, Michael S.,Hunter, A. Jacqueline,Johnson, Christopher N.,Nash, David J.,Thewlis, Kevin M.,Vong, Antonio K. K.,Austin, Nigel E.,Jeffrey, Phillip,Avenell, Kim Y.,Boyfield, Izzy,Hagan, Jim J.,Middlemiss, Derek N.,Reavill, Charlie,Riley, Graham J.,Routledge, Carole,Wood, Martyn. "Design and synthesis of trans-N-[4-[2-(6-cyano-1,2,3,4- tetrahydroisoquinolin-2-yl)ethyl]cyclohexyl]-4-quinolinecarboxamide (SB- 277011): A potent and selective dopamine D3 receptor antagonist with high oral bioavailability and CNS penetration ". . p. 1878 - 1885. Retrieved 2007/10/03.