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

Base Information

• Chemical Name: ethyl (1S,2R)-2-aminocyclohexane-1-carboxylate
• CAS No.: 179601-38-8
• Molecular Formula: C9H17NO2
• Molecular Weight: 171.23700
• DSSTox Substance ID: DTXSID50355895
• Nikkaji Number: J868.835D
• Wikidata: Q82134977
• Mol file: 179601-38-8.mol

Synonyms:179601-38-8;ethyl (1S,2R)-2-aminocyclohexane-1-carboxylate;(1S,2R)-Ethyl 2-aminocyclohexanecarboxylate;ethyl(1s,2r)-2-aminocyclohexanecarboxylate;Cyclohexanecarboxylic acid, 2-amino-, ethyl ester, (1S,2R)-;SCHEMBL2923;DTXSID50355895;(1S,2R)-Ethyl2-aminocyclohexanecarboxylate;CS-0184551;Ethyl (1S,2R)-2-aminocyclohexanecarboxylate;EN300-203726

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

Chemical Property:

• PSA: 52.32000
• LogP: 1.76730
• 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:

99.90% ^*data from raw suppliers

(1S,2R)-Ethyl2-aminocyclohexanecarboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

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

There total 5 articles about ethyl (1S,2R)-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: 74.0%

(1S,2R,αR)-2--1-carbethoxycyclohexane (163705-86-0) → (1S,2R)-2-aminocyclohexanecarboxylic acid ethyl ester (179601-38-8)

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol; water; acetic acid; Ambient temperature;

DOI:10.1021/jo960107y

Reference yield:

(-)-(6R)-6-[(1S)-1-phenylethylamino]cyclohex-1-enecarboxylic acid ethyl ester → (1S,2R)-2-aminocyclohexanecarboxylic acid ethyl ester (179601-38-8) + trans-2-amino-1-cyclohexyl carboxylic acid ethyl ester (26849-62-7)

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:

ethyl (-)-N-<(R)-1-phenylethyl>-1-aminocyclohexene-2-carboxylate (121506-74-9) → (1S,2R)-2-aminocyclohexanecarboxylic acid ethyl ester (179601-38-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / NaHB(OAc)3 / acetic acid; acetonitrile / 4 h / 0 °C

2: 74 percent / H₂ / Pd(OH)2/C / methanol; H₂O; acetic acid / Ambient temperature

With hydrogen; sodium tris(acetoxy)borohydride; palladium dihydroxide; In methanol; water; acetic acid; acetonitrile;

DOI:10.1021/jo960107y

upstream raw materials:

(1S,2R,αR)-2--1-carbethoxycyclohexane

6-(diethoxyphosphoryloxy)cyclohex-1-enecarboxylic acid ethyl ester

ethyl (-)-N-<(R)-1-phenylethyl>-1-aminocyclohexene-2-carboxylate

Downstream raw materials:

((1S,2R)-2-aminocyclohexyl)methanol

Refernces

• 1、 Cimarelli, Cristina,Palmieri, Gianni. "Stereoselective reduction of enantiopure β-enamino esters by hydride: A convenient synthesis of both enantiopure β-amino esters". . p. 5557 - 5563. Retrieved 2007/10/03.