3-AMINO-8-BENZYL-8-AZABICYCLO[3.2.1]OCTANE (3-EXO)- Chemical Properties

Boiling point:

110-115 °C(Press: 0.05 Torr)

Density 

1.082±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

10.23±0.20(Predicted)

form 

Oil

color 

Clear Light yellow to Beige

3-AMINO-8-BENZYL-8-AZABICYCLO[3.2.1]OCTANE (3-EXO)- Usage And Synthesis

Uses

Intermediate in the preparation of CCR5 receptor antagonists, antibacterial agents and dopamine antagonists

Synthesis

General procedure for the synthesis of exo-8-benzyl-8-azabicyclo[3.2.1]octan-3-one oxime from 8-benzyl-8-azabicyclo[3.2.1]octan-3-amine:[105] 8-benzyl-8-azabicyclo[3.2.1]octan-3-one oxime (7.65 g, 33 mmol) was dissolved in 1-pentanol (130 mL) at 120 °C. Sodium metal (7.6 g, 0.33 mol, 10.0 eq.) was added in batches over 2 hours. The mixture was stirred and heated under reflux conditions for 5 hours, then cooled to 5°C. The reaction mixture was slowly acidified with 6 M HCl until the pH reached acidic, and then the aqueous phase was further extracted with 6 M HCl (3 x 100 mL). The aqueous layer was gradually alkalized to pH 10 by addition of 5 M NaOH. the resulting aqueous solution was extracted with EtOAc (3 × 100 mL). The organic extracts were combined, dried with MgSO4, filtered and concentrated in vacuum. The crude product was purified by column chromatography (5-10% MeOH/CH2Cl2) to afford pure exo-8-benzyl-8-azabicyclo[3.2.1]octan-3-amine as a solid (2.60 g, 36%).

References

[1] Journal of Medicinal Chemistry, 2018, vol. 61, # 11, p. 5020 - 5033
[2] Journal of Heterocyclic Chemistry, 1982, vol. 19, # 3, p. 485 - 488
[3] Patent: WO2008/63600, 2008, A2. Location in patent: Page/Page column 11-12; 26
[4] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 2, p. 133 - 137
[5] Medicinal Chemistry Research, 2018, vol. 27, # 8, p. 1906 - 1928

3-AMINO-8-BENZYL-8-AZABICYCLO[3.2.1]OCTANE (3-EXO)-(76272-36-1)Related Product Information

• 5-Pyrimidinecarboxamide, 2-amino-N-(8-(p-fluorobenzyl)-3-beta-nortropa nyl)-4-methoxy-, monomaleate
• 5-Pyrimidinecarboxamide, N-(8-benzyl-3-beta-nortropanyl)-2-ethyl-4-met hoxy-
• 5-Pyrimidinecarboxamide, 2-amino-N-(8-benzyl-3-beta-nortropanyl)-4-met hoxy-
• 2-Amino-4-methoxy-N-(8-(p-nitrobenzyl)-3-beta-nortropanyl)-5-pyrimidin ecarboxamide maleate
• 2-Amino-4-methoxy-N-(8-(o-methylbenzyl)-3-beta-nortropanyl)-5-pyrimidi necarboxamide
• 5-Pyrimidinecarboxamide, N-(8-benzyl-3-beta-nortropanyl)-2-(dimethylam ino)-4-ethoxy-, monomaleate
• 2-Amino-N-(8-(o-fluorobenzyl)-3-beta-nortropanyl)-4-methoxy-5-pyrimidi necarboxamide
• 5-Pyrimidinecarboxamide, 4-methoxy-N-(8-(phenylmethyl)-8-azabicyclo(3. 2.1)oct-3-yl)-, exo-
• 2-Amino-N-(8-benzyl-3-beta-nortropanyl)-4-ethoxy-5-pyrimidinecarboxami de maleate
• 5-Pyrimidinecarboxamide, N-(8-benzyl-3-beta-nortropanyl)-2-(dimethylam ino)-4-methoxy-, monomaleate
• 5-Pyrimidinecarboxamide, N-(8-benzyl-3-beta-nortropanyl)-4-ethoxy-2-et hyl-
• 2-Amino-N-(8-(m-chlorobenzyl)-3-beta-nortropanyl)-4-methoxy-5-pyrimidi necarboxamide
• exo-5-Bromo-2,3-dimethoxy-N-(8-(phenylmethyl)-8-azabicyclo(3.2.1)oct-3 -yl)benzamide
• 5-Pyrimidinecarboxamide, 4-ethoxy-N-(8-(phenylmethyl)-8-azabicyclo(3.2 .1)oct-3-yl)-, exo-
• 2-Amino-N-(8-(p-chlorobenzyl)-3-beta-nortropanyl)-4-methoxy-5-pyrimidi necarboxamide
• Benzamide, 4-amino-5-bromo-N-(8-((3,4-dichlorophenyl)methyl)-8-azabicy clo(3.2.1)oct-3-yl)-2-methoxy-, exo-
• Benzamide, 4-amino-5-bromo-N-(8-((4-ethylphenyl)methyl)-8-azabicyclo(3 .2.1)oct-3-yl)-2-methoxy-, exo-
• 2-Amino-4-methoxy-N-(8-(p-methylbenzyl)-3-beta-nortropanyl)-5-pyrimidi necarboxamide