cis-3-Aminocyclohexanol hydrochloride

Base Information

• Chemical Name: cis-3-Aminocyclohexanol hydrochloride
• CAS No.: 124555-44-8
• Molecular Formula: C₆H₁₃NO*ClH
• Molecular Weight: 151.636
• European Community (EC) Number: 873-302-0
• DSSTox Substance ID: DTXSID90480731
• Mol file: 124555-44-8.mol

Synonyms:cis-3-aminocyclohexanol hydrochloride;124555-44-8;1849594-88-2;(1R,3S)-3-aminocyclohexan-1-ol hydrochloride;(1R,3S)-3-Amino-cyclohexanol hydrochloride;(1R,3S)-3-Aminocyclohexanol hydrochloride;cis-3-Amino-cyclohexanol hydrochloride;(1R,3S)-3-aminocyclohexan-1-ol;hydrochloride;C6H14ClNO;cis-3-aminocyclohexanol HCl;MFCD22689399;MFCD11870212;SCHEMBL2145087;DTXSID90480731;NJGXTVICXVECGR-RIHPBJNCSA-N;(1R,3S)-3-Aminocyclohexanol HCl;AMY37601;AS-0799;AT10758;(1R,3S)-3-Aminocyclohexan-1-Ol HCl;(1R,3S)-3-Aminocyclohexanolhydrochloride;AS-83981;CS-0042346;EN300-212435;Cis-(1R,3S)-3-amino-cyclohexanol hydrochloride;rel-(1R,3S)-3-aminocyclohexan-1-ol hydrochloride;Cyclohexanol, 3-amino-, hydrochloride, cis- (9CI)

Chemical Property of cis-3-Aminocyclohexanol hydrochloride

Chemical Property:

• PSA: 46.25000
• LogP: 1.75090
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility.: Methanol (Slightly), Water (Slightly)
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 151.0763918
• Heavy Atom Count: 9
• Complexity: 74.9

Purity/Quality:

98%Min ^*data from raw suppliers

(1S,3R)-3-AminocyclohexanolHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(CC(C1)O)N.Cl
• Isomeric SMILES: C1C[C@@H](C[C@@H](C1)O)N.Cl
• Uses: (1S,3R)-3-Aminocyclohexanol Hydrochloride is used as a reactant in the preparation of isoxazole carboxamide compounds as potent, soluble, orally active TRPV1 antagonists and analgesics.

Technology Process of cis-3-Aminocyclohexanol hydrochloride

There total 9 articles about cis-3-Aminocyclohexanol hydrochloride 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: 93.0%

C11H21NO3 (1425253-99-1,1638744-95-2) → (+/-)-cis-3-amino-cyclohexanol; hydrochloride (124555-43-7,124555-44-8,1849594-88-2)

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃; for 1h;

Reference yield:

(3-oxo-cyclohexyl)-carbamic acid tert-butyl ester (885280-38-6,1803033-61-5,1383797-87-2) → (+/-)-cis-3-amino-cyclohexanol; hydrochloride (124555-43-7,124555-44-8,1849594-88-2)

Guidance literature:

Multi-step reaction with 4 steps

1: L-Selectride / tetrahydrofuran / 2 h / -78 °C

2: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 16 h / 0 - 25 °C

3: potassium carbonate / methanol / 16 h / 20 °C

4: hydrogenchloride / methanol / 1 h / 20 °C

With hydrogenchloride; L-Selectride; potassium carbonate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol;

Reference yield:

2-cyclohex-2-enyl-isoindole-1,3-dione (1541-26-0) → (+/-)-cis-3-amino-cyclohexanol; hydrochloride (124555-43-7,124555-44-8,1849594-88-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / NBS / CHCl₃; ethanol / 8 h / Ambient temperature

2: 98 percent / 2 M HCl / methanol / 0.5 h / Ambient temperature

3: 80 percent / tributyltin hydride, AIBN / toluene; methanol / 1 h / Heating

4: 1.) hydrazine hydrate, 2.) conc. HCl / 1.) 95 percent ethanol, reflux, 2 h, 2.) room temperature

With hydrogenchloride; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; hydrazine hydrate; In methanol; ethanol; chloroform; toluene;

upstream raw materials:

(+/-)-cis-2-(3-hydroxycyclohexyl)isoindole-1,3-dione

2-cyclohex-2-enyl-isoindole-1,3-dione

1,2-trans-2,3-trans-2-bromo-3-N-phthalimidocyclohexanol

(2RS,6SR,12bSR,13RS)-13-bromo-12b-ethoxy-2,6-methanol<1,3>oxazocino<2,3-a>iso-indol-8-one

Refernces

• 1、 Sammes, Peter G.,Thetford, Dean. "Stereocontrolled Preparation of Cyclohexane Amino Alcohols Utilising a Modified Mitsunobu Reaction". . p. 655 - 661. Retrieved 2007/10/02.