rel-(1R,3S,4S,5S,7S)-4-Aminoadamantan-1-ol

Base Information

• Chemical Name: rel-(1R,3S,4S,5S,7S)-4-Aminoadamantan-1-ol
• CAS No.: 62058-03-1
• Molecular Formula: C10H17NO
• Molecular Weight: 167.251
• Hs Code.: 2922199090
• DSSTox Substance ID: DTXSID30426173
• Wikidata: Q72437747
• Mol file: 62058-03-1.mol

Synonyms:(1R,3S,4S,5S,7S)-rel-4-Aminoadamantan-1-ol;62058-03-1;rel-(1R,3S,4S,5S,7S)-4-Aminoadamantan-1-ol;DTXSID30426173;AKOS015999731

Chemical Property of rel-(1R,3S,4S,5S,7S)-4-Aminoadamantan-1-ol

Chemical Property:

• Melting Point: 230-235 °C
• Boiling Point: 275.619 °C at 760 mmHg
• PKA: 15.14±0.40(Predicted)
• Flash Point: 120.49 °C
• PSA: 46.25000
• Density: 1.205 g/cm³
• LogP: 1.58500
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 167.131014166
• Heavy Atom Count: 12
• Complexity: 200

Purity/Quality:

99%min ^*data from raw suppliers

trans-4-Aminoadamantan-1-ol 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2CC3CC(C2)(CC1C3N)O
• Isomeric SMILES: C1[C@H]2CC3(C[C@@H](C2N)CC1C3)O

Technology Process of rel-(1R,3S,4S,5S,7S)-4-Aminoadamantan-1-ol

There total 7 articles about rel-(1R,3S,4S,5S,7S)-4-Aminoadamantan-1-ol 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: 98.0%

benzyl [(1R,2s,3S,5s,7s)-5-hydroxyadamantan-2-yl]carbamate → (1u202fs,3R,4s,5S,7s)-4-aminoadamantan-1-ol (62058-03-1,62058-13-3)

Guidance literature:

With hydrogen; In methanol; at 20 ℃; for 5h;

DOI:10.1016/j.bmc.2018.08.005

Reference yield:

4-((E)-(1-phenylethylidene)amino)adamantan-1-ol → (1u202fs,3R,4r,5S,7s)-4-aminoadamantan-1-ol (62058-13-3) + (1u202fs,3R,4s,5S,7s)-4-aminoadamantan-1-ol (62058-03-1,62058-13-3)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; for 12h; under 760.051 Torr; Overall yield = 67 %; Overall yield = 0.13 g;

DOI:10.1371/journal.pone.0113841

Reference yield:

C17H23NO → (1u202fs,3R,4s,5S,7s)-4-aminoadamantan-1-ol (62058-03-1,62058-13-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; for 2.5h;

upstream raw materials:

N-(2-adamantyl)amine

4-aminoadamantan-1-ol

Downstream raw materials:

4-{[(1R,2s,3S,5s,7s)-5-hydroxy-2-adamantyl]amino}-1H-pyrrolo[2,3-b]pyridine-5-carboxamide

Refernces

• 1、 Hamaguchi, Hisao,Amano, Yasushi,Moritomo, Ayako,Shirakami, Shohei,Nakajima, Yutaka,Nakai, Kazuo,Nomura, Naoko,Ito, Misato,Higashi, Yasuyuki,Inoue, Takayuki. "Discovery and structural characterization of peficitinib (ASP015K) as a novel and potent JAK inhibitor". . p. 4971 - 4983. Retrieved 2018.
• 2、 -. "PROCESS FOR PRODUCTION OF HYDROXYADAMANTANEAMINE". Page/Page column 21-22. . Retrieved 2009/09/05.