ethyl (1S,2S)-2-aminocyclohexane-1-carboxylate

Base Information

• Chemical Name: ethyl (1S,2S)-2-aminocyclohexane-1-carboxylate
• CAS No.: 24716-94-7
• Molecular Formula: C9H17NO2
• Molecular Weight: 171.239
• DSSTox Substance ID: DTXSID601260061
• Nikkaji Number: J2.506.560C
• Mol file: 24716-94-7.mol

Synonyms:ethyl (1S,2S)-2-aminocyclohexane-1-carboxylate;24716-94-7;(1S,2S)-2-Aminocyclohexane-1-carboxylic acid ethyl ester;cyclohexanecarboxylic acid, 2-amino-, ethyl ester, (1s,2s)-;(1S,2S)-2-aMinocyclohexanecarboxylic acid ethyl ester;SCHEMBL195;DTXSID601260061;Ethyl (1S,2S)-2-aminocyclohexanecarboxylate;F53563;EN300-19662811

Chemical Property of ethyl (1S,2S)-2-aminocyclohexane-1-carboxylate

Chemical Property:

• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 171.125928785
• Heavy Atom Count: 12
• Complexity: 159

Purity/Quality:

98%min ^*data from raw suppliers

(1S,2S)-Ethyl2-aminocyclohexanecarboxylateHCl 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C1CCCCC1N
• Isomeric SMILES: CCOC(=O)[C@H]1CCCC[C@@H]1N

Technology Process of ethyl (1S,2S)-2-aminocyclohexane-1-carboxylate

There total 10 articles about ethyl (1S,2S)-2-aminocyclohexane-1-carboxylate 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:

(-)-(6S)-6-[(1S)-1-phenylethylamino]cyclohex-1-enecarboxylic acid ethyl ester → (1S,2S)-2-aminocyclohexanecarboxylic acid ethyl ester (24716-94-7) + (1R,2S)-2-aminocyclohexanecarboxylic acid ethyl ester (192047-04-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 48h; Title compound not separated from byproducts;

DOI:10.1016/j.tet.2004.12.008

Reference yield:

6-carbamoylcyclohex-3-enecarboxylic acid (1469-49-4,2028-12-8) → ethyl cis-2-amino-1-cyclohexanecarboxylate (1436-60-8,1436-61-9,24716-94-7,26849-62-7,64162-07-8,75197-07-8,115014-75-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / H₂ / 10percent Pt/C / ethanol / 760 Torr / Ambient temperature

2: 1.) bromine, NaOH; 2.) HCl / 1.) water, 75 deg C, 2 min; 2.) reflux, 3 h

With hydrogenchloride; sodium hydroxide; hydrogen; bromine; platinum on activated charcoal; In ethanol;

DOI:10.1016/S0040-4020(01)85926-3

Reference yield:

ethyl 2-aminocyclohex-1-ene-1-carboxylate (1128-00-3) → ethyl cis-2-amino-1-cyclohexanecarboxylate (1436-60-8,1436-61-9,24716-94-7,26849-62-7,64162-07-8,75197-07-8,115014-75-0)

Guidance literature:

With sodium cyanoborohydride; acetic acid; In ethyl acetate; at 0 ℃; for 6h;

DOI:10.1002/adsc.201300982

upstream raw materials:

ethanol

(+)-(S,S)-N-benzoyl-trans-2-aminocyclohexanecarboxylic acid

ethyl trans-2-amino-1-cyclohexanecarboxylate

(+/-)-N-benzoyl-trans-2-aminocyclohexane-carboxylic acid

Downstream raw materials:

(+/-)-cis-2-(2-ethoxycarbonyl-ethylamino)-cyclohexane-carboxylic acid-⁽¹⁾-ethyl ester

cis-2-aminocyclohexane-1-carboxamide

trans-2-aminocyclohexane-1-carboxamide

cis-2-aminocyclohexanecarbohydrazide