N-((1R,3s,5S)-8-Benzyl-8-azabicyclo[3.2.1]octan-3-yl)isobutyramide

Base Information

• Chemical Name: N-((1R,3s,5S)-8-Benzyl-8-azabicyclo[3.2.1]octan-3-yl)isobutyramide
• CAS No.: 376348-67-3
• Molecular Formula: C18H26N2O
• Molecular Weight: 286.417
• European Community (EC) Number: 609-457-6
• UNII: 82P8FGU668,9XXZ53Z6T8
• DSSTox Substance ID: DTXSID701138942,DTXSID401141974
• Mol file: 376348-67-3.mol

Synonyms:376348-67-3;N-((1R,3s,5S)-8-Benzyl-8-azabicyclo[3.2.1]octan-3-yl)isobutyramide;N-(8-Benzyl-8-azabicyclo[3.2.1]oct-3-yl-exo)-2-methylpropanamide;exo-N-(8-Benzyl-8-azabicyclo[3.2.1]octan-3-yl)isobutyramide;N-[(1R,5S)-8-benzyl-8-azabicyclo[3.2.1]octan-3-yl]-2-methylpropanamide;858651-21-5;2-Methyl-N-[(3-endo)-8-(phenylmethyl)-8-azabicyclo[3.2.1]oct-3-yl]propanamide;2-Methyl-N-[(3-exo)-8-(phenylmethyl)-8-azabicyclo[3.2.1]oct-3-yl]propanamide;9XXZ53Z6T8;SCHEMBL13915687;82P8FGU668;DTXSID401141974;DTXSID701138942;MFCD16657117;AKOS015998976;AKOS025396691;N-[(1S,5R)-8-benzyl-8-azabicyclo[3.2.1]octan-3-yl]-2-methylpropanamide;AS-71839;CS-0078636;N-[(1R,3S,5S)-8-BENZYL-8-AZABICYCLO[3.2.1]OCTAN-3-YL]-2-METHYLPROPANAMIDE;Propanamide, 2-methyl-N-[(3-endo)-8-(phenylmethyl)-8-azabicyclo[3.2.1]oct-3-yl]-;Propanamide, 2-methyl-N-[(3-exo)-8-(phenylmethyl)-8-azabicyclo[3.2.1]oct-3-yl]-

Chemical Property of N-((1R,3s,5S)-8-Benzyl-8-azabicyclo[3.2.1]octan-3-yl)isobutyramide

Chemical Property:

• Appearance/Colour: Light yellow solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 138-140 °C
• Refractive Index: 1.567
• Boiling Point: 449.068 °C at 760 mmHg
• PKA: 15.65±0.20(Predicted)
• Flash Point: 225.388 °C
• PSA: 32.34000
• Density: 1.09 g/cm³
• LogP: 3.28300
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Dichloromethane
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 286.204513457
• Heavy Atom Count: 21
• Complexity: 348

Purity/Quality:

98% ^*data from raw suppliers

N-(8-Benzyl-8-azabicyclo[3.2.1]oct-3-yl-exo)-2-methylpropanamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(=O)NC1CC2CCC(C1)N2CC3=CC=CC=C3
• Isomeric SMILES: CC(C)C(=O)NC1C[C@H]2CC[C@@H](C1)N2CC3=CC=CC=C3

Technology Process of N-((1R,3s,5S)-8-Benzyl-8-azabicyclo[3.2.1]octan-3-yl)isobutyramide

There total 10 articles about N-((1R,3s,5S)-8-Benzyl-8-azabicyclo[3.2.1]octan-3-yl)isobutyramide 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%

8-benzyl-8-aza-bicyclo[3.2.1]oct-3-yl-amine (76272-36-1) + isobutyryl chloride (79-30-1) → exo-N-(8-benzyl-8-azabicyclo[3.2.1]oct-3-yl)-2-methylpropanamide (376348-67-3)

Guidance literature:

With sodium carbonate; In dichloromethane; water; at 0 - 20 ℃; for 2.5h;

Reference yield: 93.0%

8-benzyl-8-azabicyclo[3.2.1]octan-3-amine + isobutyryl chloride (79-30-1) → exo-N-(8-benzyl-8-azabicyclo[3.2.1]oct-3-yl)-2-methylpropanamide (376348-67-3)

Guidance literature:

With sodium carbonate; In dichloromethane; at 0 - 20 ℃; for 2.5h;

DOI:10.1021/acs.orglett.8b02087

Reference yield: 77.0%

8-benzyl-8-aza-bicyclo[3.2.1]oct-3-yl-amine (76272-36-1) + isobutyryl chloride (513-36-0) → exo-N-(8-benzyl-8-azabicyclo[3.2.1]oct-3-yl)-2-methylpropanamide (376348-67-3)

Guidance literature:

With potassium carbonate; In dichloromethane; water; at 0 - 20 ℃; for 3h;

upstream raw materials:

8-benzyl-8-aza-bicyclo[3.2.1]oct-3-yl-amine

isobutyryl chloride

isobutyryl chloride

8-benzyl-8-azabicyclo[3.2.1] octan-3-one oxime

Downstream raw materials:

exo-8-benzyl-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane

UK-408027

1-acetyl-N-(3-chloro-4-methylphenyl)-N-(3-(3-exo-(3-isopropyl-5-methyl-4-hydro-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]oct-8-yl)propyl)-4-piperidinylcarboxamide

4,4-difluoro-N-[(1S)-3-[(1R,5S)-3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-phenylpropyl]cyclohexane-1-carboxamide

Refernces

• 1、 Li, Dongmei,Tan, Yu,Peng, Lei,Li, Shan,Zhang, Nan,Liu, Yidong,Yan, Hailong. "Asymmetric Mannich Reaction and Construction of Axially Chiral Sulfone-Containing Styrenes in One Pot from α-Amido Sulfones Based on the Waste-Reuse Strategy". supporting information. p. 4959 - 4963. Retrieved 2018/08/24.
• 2、 -. "AMIDE COMPOUNDS, THEIR PHARMACEUTICAL COMPOSITIONS, THEIR PREPARATION METHOD AND THEIR USES". Page/Page column 20. . Retrieved 2011/10/19.