Ethyl trans-2-[4-(Boc-aMino)cyclohexyl]acetate

Base Information

• Chemical Name: Ethyl trans-2-[4-(Boc-aMino)cyclohexyl]acetate
• CAS No.: 946598-34-1
• Molecular Formula: C15H27NO4
• Molecular Weight: 285.384
• Hs Code.: 2924299090
• Mol file: 946598-34-1.mol

Synonyms:Ethyl trans-2-[4-(Boc-aMino)cyclohexyl]acetate;Cyclohexaneacetic acid, 4-[[(1,1-diMethylethoxy)carbonyl]aMino]-, ethyl ester, trans-

Chemical Property of Ethyl trans-2-[4-(Boc-aMino)cyclohexyl]acetate

Chemical Property:

• Melting Point: 75 °C
• Boiling Point: 378.0±11.0 °C(Predicted)
• PKA: 12.50±0.40(Predicted)
• PSA: 68.12000
• Density: 1.04±0.1 g/cm3(Predicted)
• LogP: 3.22750
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

98% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Ethyl 2-((1R,4R)-4-((tert-Butoxycarbonyl)amino)cyclohexyl)acetate is an intermediate for the synthesis of Desmethyl Cariprazine Hydrochloride (D291365), a derivative of Cariprazine (C183490) which is an orally active D2/D3 dopamine receptor antagonist (1,2,3). Cariprazine is an antipsychotic drug candidate for the potential treatment of schizophrenia, bipolar mania and depression.

Technology Process of Ethyl trans-2-[4-(Boc-aMino)cyclohexyl]acetate

There total 8 articles about Ethyl trans-2-[4-(Boc-aMino)cyclohexyl]acetate 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: 100.0%

2-((trans)-4-((tert-butoxycarbonyl)amino)cyclohexyl)acetic acid + ethyl iodide (75-03-6) → trans 2-{1-[4-(N-(tert-butoxycarbonyl))amino]cyclohexyl}ethyl acetate (946598-34-1)

Guidance literature:

With potassium carbonate; In acetonitrile; Reflux;

DOI:10.1021/acs.jmedchem.5b00585

Reference yield: 60.0%

2-{4-[(N-(tert-butoxycarbonyl))amino]cyclohexylidene}ethyl acetate → trans 2-{1-[4-(N-(tert-butoxycarbonyl))amino]cyclohexyl}ethyl acetate (946598-34-1)

Guidance literature:

With palladium on activated charcoal; hydrogen; In ethanol; at 20 ℃; for 10h; under 4500.45 Torr; Pressure; Inert atmosphere;

Reference yield:

2-{4-[(N-(tert-butoxycarbonyl))amino]cyclohexylidene}ethyl acetate → trans 2-{1-[4-(N-(tert-butoxycarbonyl))amino]cyclohexyl}ethyl acetate (946598-34-1) + ethyl 2-(cis-4-((tert-butoxycarbonyl)amino)cyclohexyl)acetate

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In tetrahydrofuran; water; at 20 ℃; for 20h; under 760.051 Torr; Large scale;

DOI:10.1021/acs.oprd.9b00182

upstream raw materials:

trans-2-(4-aminocyclohexyl)acetic acid

4-nitrobenzeneacetic acid

ethyl iodide

N-(tert-butoxycarbonyl)-4-aminocyclohexanone

Downstream raw materials:

trans-2-(1-(4-(N-tert-butoxycarbonyl)amino)cyclohexyl)acetaldehyde

Cariprazine

trans-2-(2-(1-4-(N-tert-butyloxycarbonyl)amino)cyclohexyl)ethyl-7-cyano-1,2,3,4-tetrahydroisoquinoline

trans-4-(2-(4-(2,3-dichlorophenyl)piperazin-1-yl)ethyl)cyclohexane-1-amine