trans-4-Morpholinocyclohexanol

Base Information

• Chemical Name: trans-4-Morpholinocyclohexanol
• CAS No.: 1228947-14-5
• Molecular Formula: C10H19NO2
• Molecular Weight: 185.266
• Hs Code.: 2934999090
• Mol file: 1228947-14-5.mol

Synonyms:4-morpholin-4-ylcyclohexan-1-ol;

Chemical Property of trans-4-Morpholinocyclohexanol

Chemical Property:

• PSA: 32.70000
• LogP: 0.56000
• Storage Temp.: 2-8°C(protect from light)

Purity/Quality:

99% ^*data from raw suppliers

trans-4-Morpholinocyclohexanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: trans-4-Morpholinocyclohexanol is a reagent used in the preparation of quinazoline and quinoline derivatives which act as interleukin-1 receptor-associated kinases (IRAK) inhibitors.

Technology Process of trans-4-Morpholinocyclohexanol

There total 2 articles about trans-4-Morpholinocyclohexanol 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%

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + (1s,4s)-4-aminocyclohexan-1-ol hydrochloride (56239-26-0) → (1r,4r)-4-(morpholin-4-yl)cyclohexan-1-ol (1228947-14-5)

Guidance literature:

With potassium carbonate; In acetonitrile; at 60 ℃; for 16h;

DOI:10.1021/acs.jmedchem.7b01290

Reference yield:

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + trans-4-hydroxycyclohexylamine (27489-62-9) → (1r,4r)-4-(morpholin-4-yl)cyclohexan-1-ol (1228947-14-5)

Guidance literature:

With triethylamine; In acetonitrile; at 60 ℃;

Reference yield: 82.0%

(1r,4r)-4-(morpholin-4-yl)cyclohexan-1-ol (1228947-14-5) + methanesulfonyl chloride (124-63-0) → (1r,4s)-4-morpholinocyclohexyl methanesulfonate

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.7b01290

upstream raw materials:

1,1'-oxybis(2-bromo-ethane)

trans-4-hydroxycyclohexylamine

(1s,4s)-4-aminocyclohexan-1-ol hydrochloride

Downstream raw materials:

C₂₁H₂₉N₃O₃S

C₂₁H₂₇N₃O₄S

2-((R)-4-(((1r,4r)-4-morpholinocyclohexyl)oxy)-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-5-yl)acetamide

(3R)-3-[2-[(tert-butyldimethylsilyl)oxy]ethyl]-12-[[4-(morpholin-4-yl)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1⁽¹²⁾,2⁽⁶⁾,8,10-tetraene

Refernces

• 1、 Scott, James S.,Degorce, Sébastien L.,Anjum, Rana,Culshaw, Janet,Davies, Robert D.M.,Davies, Nichola L.,Dillman, Keith S.,Dowling, James E.,Drew, Lisa,Ferguson, Andrew D.,Groombridge, Sam D.,Halsall, Christopher T.,Hudson, Julian A.,Lamont, Scott,Lindsay, Nicola A.,Marden, Stacey K.,Mayo, Michele F.,Pease, J. Elizabeth,Perkins, David R.,Pink, Jennifer H.,Robb, Graeme R.,Rosen, Alan,Shen, Minhui,McWhirter, Claire,Wu, Dedong. "Discovery and Optimization of Pyrrolopyrimidine Inhibitors of Interleukin-1 Receptor Associated Kinase 4 (IRAK4) for the Treatment of Mutant MYD88L265P Diffuse Large B-Cell Lymphoma". supporting information. p. 10071 - 10091. Retrieved 2017/12/15.