tert-butyl N-[(1R,2S)-2-aminocyclohexyl]carbamate

Base Information

• Chemical Name: tert-butyl N-[(1R,2S)-2-aminocyclohexyl]carbamate
• CAS No.: 364385-54-6
• Molecular Formula: C11H22 N2 O2
• Molecular Weight: 214.308
• Hs Code.: 2924299090
• European Community (EC) Number: 690-961-8,806-388-5
• DSSTox Substance ID: DTXSID70363876
• Wikidata: Q82147629
• Mol file: 364385-54-6.mol

Synonyms:364385-54-6;tert-butyl (1R,2S)-2-aminocyclohexylcarbamate;tert-butyl N-[(1R,2S)-2-aminocyclohexyl]carbamate;tert-Butyl (cis-2-aminocyclohexyl)carbamate;184954-75-4;tert-Butyl ((1R,2S)-2-aminocyclohexyl)carbamate;MFCD09952106;Carbamic acid, [(1R,2S)-2-aminocyclohexyl]-, 1,1-dimethylethyl ester;Cis-(1S, 2R)-1N-Boc-cyclohexane-1,2-diamine;tert-Butyl [(1R,2S)-2-aminocyclohexyl]carbamate;(1R,2S)-N1-(tert-Butoxycarbonyl)-1,2-cyclohexanediamine;SCHEMBL555256;DTXSID70363876;tert-butyl N-[(1R,2S)-2-aminocyclohexyl]carbamate >97%ee;AMY16663;cis-N1-Boc-1,2-cyclohexanediamine;N-Boc-(1R,2S)-diaminocyclohexane;CX1046;AKOS007929975;N-Boc-1(R),2(S)-Diaminocyclohexane;cis-2-Amino-1-(Boc-amino)cyclohexane;SS-4352;cis-tert-Buty 2-aminocyclohexylcarbamate;cis-tert-butyl 2-aminocyclohexylcarbamate;AC-31614;(1R,2S)-N1-Boc-1,2-cyclohexanediamine;B3478;B4331;CS-0039723;CS-0137432;(1R,2S)-2-Amino-1-(Boc-amino)cyclohexane;tert-butyl(1R,2S)-2-aminocyclohexylcarbamate;EN300-1265959;EN300-3152940;(1S,2R)-2-(t-butoxycarbonylamino)cyclohexylamine;(1S,2R)-2-tert-butoxycarbonylaminocyclohexylamine;A850090;N-Boc-1(R),2(S)-diaminocyclohexane, AldrichCPR;(1s,2r)-2-tert-butoxycarbonylamino-cyclohexylamine;cis-2-Amino-1-(tert-butoxycarbonylamino)cyclohexane;(+/-)-cis-N-tert-Butoxycarbonyl-1,2-cyclohexanediamine;cis-N-(tert.-butyloxycarbonyl)-cyclohexane-1,2-diamine;rac-tert-butyl N-[(1R,2S)-2-aminocyclohexyl]carbamate;Z1505699012;(1R,2S)-2-Amino-1-(tert-butoxycarbonylamino)cyclohexane;((1R,2S)-2-Amino-cyclohexyl)-carbamic acid tert-butyl ester;(1R,2S) (2-amino-cyclohexyl)-carbamic acid tert-butyl ester;Carbamic acid,[(1R,2S)-2-aminocyclohexyl]-,1,1-dimethylethyl ester(9ci);Carbamic acid, [(1S,2R)-2-aminocyclohexyl]-, 1,1-dimethylethyl ester (9CI);tert-butyl(1S,2R)-2-aminocyclohexylcarbamate

Chemical Property of tert-butyl N-[(1R,2S)-2-aminocyclohexyl]carbamate

Chemical Property:

• Melting Point: 181-183 °C
• Boiling Point: 322.1±31.0 °C(Predicted)
• PKA: 12.26±0.40(Predicted)
• PSA: 64.35000
• Density: 1.02±0.1 g/cm3(Predicted)
• LogP: 2.87220
• Storage Temp.: 0-10°C
• Solubility.: soluble in dichloromethane
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 214.168127949
• Heavy Atom Count: 15
• Complexity: 223

Purity/Quality:

98%,99%, ^*data from raw suppliers

(1R,2S)-N1-(tert-Butoxycarbonyl)-1,2-cyclohexanediamine >98.0%(GC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1CCCCC1N
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H]1CCCC[C@@H]1N

Technology Process of tert-butyl N-[(1R,2S)-2-aminocyclohexyl]carbamate

There total 15 articles about tert-butyl N-[(1R,2S)-2-aminocyclohexyl]carbamate 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: 98.8%

tert-butyl [(1R,2S)-2-(phthalimido)cyclohexyl]-carbamate (364385-60-4) → (1S,2R)-2-tert-Butoxycarbonylamino-cyclohexylamine (364385-54-6)

Guidance literature:

With hydrazine hydrate; In ethanol; for 2h; Reflux;

DOI:10.1016/j.bmc.2008.11.012

Reference yield: 69.0%

(1S,2R)-2-(N-tert-butyloxycarbonylamino)-1-azidocyclohexane (603128-65-0) → (1S,2R)-2-tert-Butoxycarbonylamino-cyclohexylamine (364385-54-6)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In methanol; for 4h; under 1654.92 Torr;

Reference yield: 59.8%

di-tert-butyl dicarbonate (24424-99-5) + cis-cyclohexane-1,2-diamine (1436-59-5) → cis-1,2-di(tert-butoxycarbonylamino)cyclohexane (365997-18-8,155833-17-3,185854-61-9,345905-88-6) + (1S,2R)-2-tert-Butoxycarbonylamino-cyclohexylamine (364385-54-6)

Guidance literature:

cis-cyclohexane-1,2-diamine; With hydrogenchloride; In ethanol; at 0 - 5 ℃; for 2h; Inert atmosphere; Large scale;

di-tert-butyl dicarbonate; In ethanol; at 20 ℃; Inert atmosphere; Large scale;

upstream raw materials:

(1S,2R)-2-(N-tert-butyloxycarbonylamino)-1-azidocyclohexane

(1R,2R)-trans-2-azidocyclohexanol

cyclohexane-1,2-epoxide

(1R,2R)-trans-2-(N-tert-butyloxycarbonyl)amino-1-cyclohexanol

Downstream raw materials:

N-[(2R)-tert-butyloxycarbonylaminocyclohex-(1S)-yl]-N-(chloroacetyl)glycine ethyl ester

N-[(2R)-tert-butyloxycarbonylaminocyclohex-(1S)-yl]-N-(thymin-1-ylacetyl)glycine ethyl ester

tert-butyl ((1S,2R)-2-aminocyclohexyl)carbamate

4-(3-(2H-1,2,3-triazol-2-yl)phenylamino)-2-((1R, 2S)-2-aminocyclohexylamino)pyrimidine-5-carboxamide acetic acid salt

Refernces

• 1、 Okano, Masahiko,Mito, Jun,Maruyama, Yasufumi,Masuda, Hirofumi,Niwa, Tomoko,Nakagawa, Shin-ichiro,Nakamura, Yoshitaka,Matsuura, Akira. "Discovery and structure-activity relationships of 4-aminoquinazoline derivatives, a novel class of opioid receptor like-1 (ORL1) antagonists". experimental part. p. 119 - 132. Retrieved 2011/02/25.
• 2、 Govindaraju,Kumar, Vaijayanti A.,Ganesh, Krishna N.. "Synthesis and Evaluation of (1S,2R/1R,2S)-Aminocyclohexylglycyl PNAs As Conformationally Preorganized PNA Analogues for DNA/RNA Recognition". . p. 1858 - 1865. Retrieved 2007/10/03.