275815-60-6

Basic information

• Product Name: Carbamic acid, [(1R,2R)-2-formylcyclohexyl]-, phenylmethyl ester
• CAS NO: 275815-60-6
• Molecular Formula: C15H19NO3
• Molecular Weight: 261.321
• Mol File: 275815-60-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [(1R,2R)-2-formylcyclohexyl]-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [(1R,2R)-2-formylcyclohexyl]-, phenylmethyl ester(275815-60-6)
• EPA Substance Registry System: Carbamic acid, [(1R,2R)-2-formylcyclohexyl]-, phenylmethyl ester(275815-60-6)

Safety Data

• Hazardous Substances Data: 275815-60-6(Hazardous Substances Data)

Upstream product

• 501-53-1 benzyl chloroformate 
• 178112-24-8 [(1R,2R)-2-((R)-1-Phenyl-ethylamino)-cyclohexyl]-methanol 
• 163877-12-1 (R,R,R)-2--1-carbethoxycyclohexane 
• 163705-86-0 (1S,2R,αR)-2--1-carbethoxycyclohexane 
• 121506-74-9 ethyl (-)-N-<(R)-1-phenylethyl>-1-aminocyclohexene-2-carboxylate 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 
• 100-51-6 benzyl alcohol 
• 13149-00-3 1,2-cis-cyclohexanedicarboxylic anhydride 
• 17488-76-5 C₁₀H₁₆O₄ 
• 17488-76-5 (1S,2R)-Cyclohexane-1,2-dicarboxylic acid monoethyl ester 
• 155080-10-7 oxallyl chloride 
• 213672-84-5 trans-(1R,2R)-1-(benzyloxycarbonylamino)-2-hydroxymethyl-cyclohexane 
• 178737-10-5 trans-(1R,2R)-1-amino-2-hydroxymethyl-cyclohexane 

Downstream Products

• 383430-26-0 {(1R,2S)-2-[(S)-3-(4-Fluoro-benzyl)-piperidin-1-ylmethyl]-cyclohexyl}-carbamic acid benzyl ester 
• 275812-32-3 N-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-N'-((1R,2S)-2-{[3(S)-(4-fluorobenzyl)piperidinyl]methyl}cyclohexyl)urea 
• 852660-37-8 N-((1R,2S)-2-{[tert-butoxycarbonyl[3-(4-fluorophenyl)propyl]amino]methyl}cyclohexyl)-N'-[3-(1-methyl-1H-tetrazol-5-yl)phenyl]urea 
• 852660-52-7 N-[3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)phenyl]-N'-((1R,2S)-2-{[((2RS)-6-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl)amino]methyl}cyclohexyl)urea 
• 852660-57-2 N-[3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)phenyl]-N'-((1R,2S)-2-{[((2RS)-6-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl)(methyl)amino]methyl}cyclohexyl)urea 
• 852660-58-3 benzyl ((1R,2S)-2-{[((2RS)-6-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl)(methyl)amino]methyl}cyclohexyl)carbamate 
• 852660-36-7 (1R,2S)-2-({tert-butoxycarbonyl-[3-(4-fluorophenyl)-propyl]amino}-methyl)-cyclohexylamine 
• 852660-59-4 N-(2RS)-{[(1S,2R)-2-aminocyclohexyl]methyl}-6-fluoro-N-methyl-1,2,3,4-tetrahydronaphthalen-2-amine 
• 852660-56-1 N-{[(1S,2R)-2-aminocyclohexyl]methyl}-(2RS)-6-fluoro-1,2,3,4-tetrahydronaphthalen-2-amine 
• 852660-32-3 N-((1R,2S)-2-{[[3-(4-fluorophenyl)propyl]amino]methyl}cyclohexyl)-N'-[3-(1-methyl-1H-tetrazol-5-yl)phenyl]urea 
• 852660-55-0 benzyl ((1R,2S)-2-{[((2RS)-6-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl)amino]methyl}cyclohexyl)carbamate 
• 852660-49-2 (2-{[3-(4-fluorophenyl)-2,2-dimethylpropylamino]methyl}cyclohexyl)-carbamic acid benzyl ester 
• 852660-34-5 (1R,2S)-[2-({[3-(4-fluoro-phenyl)-propyl]amino}-methyl)-cyclohexyl]-carbamic acid benzyl ester 

Relevant articles and documents

Stereoselective process for a CCR3 antagonist

A convergent, multikilogram, stereoselective synthesis of 1 is described. A key fragment, (S)-3-(4-fluorobenzyl)piperidine (2) was synthesized from valerolactam in three steps using our recently discovered Ir-BDPP-catalyzed asymmetric hydrogenation. Anoth

Discovery of CC chemokine receptor-3 (CCR3) antagonists with picomolar potency

Starting with our previously described20 class of CC chemokine receptor-3 (CCR3) antagonist, we improved the potency by replacing the phenyl linker of 1 with a cyclohexyl linker and by replacing the 4-benzylpiperidine with a 3-benzylpiperidine. The resulting compound, 32, is a potent and selective antagonist of CCR3. SAR studies showed that the 3-acetylphenyl urea of 32 could be replaced with heterocyclic ureas or heterocyclic-substituted phenyl ureas and still maintain the potency (inhibition of eotaxin-induced chemotaxis) of this class of compounds in the low-picomolar range (IC50 = 10-60 pM), representing some of the most potent CCR3 antagonists reported to date. The potency of 32 for mouse CCR3 (chemotaxis IC50 = 41 nM) and its oral bioavailability in mice (20% F) were adequate to assess the efficacy in animal models of allergic airway inflammation. Oral administration of 32 reduced eosinophil recruitment into the lungs in a dose-dependent manner in these animal models. On the basis of its overall potency, selectivity, efficacy, and safety profile, the benzenesulfonate salt of 32, designated DPC168, entered phase I clinical trials.