(1R,2R)-2-Aminocyclopentanol

Base Information

• Chemical Name: (1R,2R)-2-Aminocyclopentanol
• CAS No.: 68327-03-7
• Molecular Formula: C₅H₁₁NO
• Molecular Weight: 101.148
• European Community (EC) Number: 815-935-7,846-471-3
• DSSTox Substance ID: DTXSID60440241
• Nikkaji Number: J885.068B
• Wikidata: Q76415699
• ChEMBL ID: CHEMBL2375114
• Mol file: 68327-03-7.mol

Synonyms:(1R,2R)-2-Aminocyclopentanol;trans-2-aminocyclopentanol;59260-76-3;68327-03-7;(1R,2R)-2-aminocyclopentan-1-ol;trans-2-Aminocyclpentanol;trans-2-Amino-cyclopentanol;Cyclopentanol, 2-amino-, (1R,2R)-;Cyclopentanol, 2-amino-, (1R,2R)-rel-;Cyclopentanol, trans-2-amino-;MFCD08669809;trans 2-aminocyclopentanol;trans-2-aminocy-clopentanol;(R,R)-2-aminocyclopentanol;trans-2- amino-cyclopentanol;SCHEMBL553132;Trans-2-hydroxycyclopentylamine;CHEMBL2375114;2alpha-Aminocyclopentan-1beta-ol;DTXSID60440241;JFFOUICIRBXFRC-RFZPGFLSSA-N;(+/-) trans-2-aminocyclopentanol;(+/-)-trans-2-aminocyclopentanol;trans-1-amino-2-hydroxycyclopentane;(1R,2R)-2-hydroxy-cyclopentylamine;MFCD10568161;AKOS005363022;rac-(1R,2R)-2-aminocyclopentan-1-ol;DS-12040;CS-0096407;EN300-59553;EN300-250068;CYCLOPENTANOL,2-AMINO-,(1R,2R)-(9CI);A850185;A914300

Chemical Property of (1R,2R)-2-Aminocyclopentanol

Chemical Property:

• Boiling Point: 179.4±33.0 °C(Predicted)
• PKA: 14.93±0.40(Predicted)
• PSA: 46.25000
• Density: 1.084±0.06 g/cm3(Predicted)
• LogP: 0.55880
• Storage Temp.: 2-8°C
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 101.084063974
• Heavy Atom Count: 7
• Complexity: 65.1

Purity/Quality:

98%min ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC(C(C1)O)N
• Isomeric SMILES: C1C[C@H]([C@@H](C1)O)N

Technology Process of (1R,2R)-2-Aminocyclopentanol

There total 27 articles about (1R,2R)-2-Aminocyclopentanol 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: 97.0%

(1S,2S)-trans-2-(N-benzyl)amino-1-cyclopentanol (1033605-25-2) → (1S,2S)-2-aminocyclopentanol (930-45-0,33092-86-3,33092-90-9,57070-95-8,59260-76-3,68327-03-7,89381-13-5,135969-63-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; under 760 Torr;

DOI:10.1021/jo052433w

Reference yield: 90.0%

(1S,2S)-2-(benzyloxy)cyclopentanamine (181657-56-7,404028-21-3,796038-32-9,181657-57-8) → (1S,2S)-2-aminocyclopentanol (930-45-0,33092-86-3,33092-90-9,57070-95-8,59260-76-3,68327-03-7,89381-13-5,135969-63-0)

Guidance literature:

With hydrogenchloride; hydrogen; palladium 10% on activated carbon; In methanol; water; at 25 ℃; for 14h;

Reference yield: 88.0%

(1S,2S)-trans-2-<(R)-(α-methylbenzyl)amino>cyclopentanol hydrochloride → (1S,2S)-2-aminocyclopentanol (930-45-0,33092-86-3,33092-90-9,57070-95-8,59260-76-3,68327-03-7,89381-13-5,135969-63-0)

Guidance literature:

With ammonium formate; palladium on activated charcoal; In N,N-dimethyl-formamide; at 110 - 120 ℃; for 4h;

DOI:10.1021/jo00221a036

upstream raw materials:

trans-2-aminocyclopentanol

1-azido-2-(trimethylsilyloxy)cyclopentane

benzyl (1S,2S)-trans-N-(2-hydroxycyclopentyl)carbamate

(1S,2S)-trans-2-azidocyclopentanol

Downstream raw materials:

2-phenyl-(3ar,6ac)-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazole

(1R,2R)-trans-2-(tertbutoxycarbonylamino)cyclopentanol

(1R,2S)-2-tert-Butoxycarbonylaminocyclopentylamine

3-[(2,4-difluorophenyl)amino]-N-[(1S,2S)-2-hydroxycyclopentyl]-6-oxo-7-phenyl-6,7-dihydrothieno[2,3-b]pyridine-2-carboxamide

Refernces

• 1、 Birrell, James A.,Jacobsen, Eric N.. "A practical method for the synthesis of highly enantioenriched trans -1,2-amino alcohols". . p. 2895 - 2897. Retrieved 2013/07/26.
• 2、 Schiffers, Ingo,Rantanen, Toni,Schmidt, Frank,Bergmans, Werner,Zani, Lorenzo,Bolm, Carsten. "Resolution of racemic 2-aminocyclohexanol derivatives and their application as ligands in asymmetric catalysis". . p. 2320 - 2331. Retrieved 2007/10/03.