endo-8-Isopropyl-8-azabicyclo[3.2.1]octan-3-ol

Base Information

• Chemical Name: endo-8-Isopropyl-8-azabicyclo[3.2.1]octan-3-ol
• CAS No.: 3423-25-4
• Molecular Formula: C10H19 N O
• Molecular Weight: 169.267
• Hs Code.: 2933990090
• European Community (EC) Number: 222-314-9
• Nikkaji Number: J205.518J
• Mol file: 3423-25-4.mol

Synonyms:endo-8-Isopropyl-8-azabicyclo[3.2.1]octan-3-ol;3423-25-4;(3-endo)-8-(1-Methylethyl)-8-azabicyclo[3.2.1]octan-3-ol;N-Isopropylnortropine;SCHEMBL13676329;SCHEMBL18959372;SCHEMBL21145769;AKOS040768828;BS-44769;CS-0197164;rac-(1R,5S)-8-isopropyl-8-azabicyclo[3.2.1]octan-3-ol

Chemical Property of endo-8-Isopropyl-8-azabicyclo[3.2.1]octan-3-ol

Chemical Property:

• Vapor Pressure: 0.00115mmHg at 25°C
• Boiling Point: 266.9±15.0℃ (760 Torr)
• PKA: 14.84±0.20(Predicted)
• Flash Point: 89.7±14.5℃
• PSA: 23.47000
• Density: 1.037±0.06 g/cm3 (20 ºC 760 Torr)
• LogP: 1.32040
• Storage Temp.: Room Temperature
• Solubility.: Dichloromethane; Ethyl Acetate
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 169.146664230
• Heavy Atom Count: 12
• Complexity: 155

Purity/Quality:

99% ^*data from raw suppliers

8-Isopropyl-8-azabicyclo[3.2.1]octan-3-ol 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)N1C2CCC1CC(C2)O
• Isomeric SMILES: CC(C)N1[C@@H]2CC[C@H]1CC(C2)O
• Uses: (1R,5S)-8-Isopropyl-8-azabicyclo[3.2.1]octan-3-ol is an intermediate for the synthesis of (S)-(1R,3r,5S)-8-Isopropyl-8-azabicyclo[3.2.1]octan-3-yl 3-Hydroxy-2-phenylpropanoate (I824270), which is a compound that can be synthesized from Atropine (A794630), a nerve agent that occurs naturally in plants of the nightshade family.

Technology Process of endo-8-Isopropyl-8-azabicyclo[3.2.1]octan-3-ol

There total 5 articles about endo-8-Isopropyl-8-azabicyclo[3.2.1]octan-3-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: 40.0%

(1R,3R,5S)-3-Hydroxy-8-isopropyl-8-methyl-8-azonia-bicyclo[3.2.1]octane; iodide (93713-44-1) → endo-8-(1-methylethyl)-8-azabicyclo<3.2.1>octan-3-ol (3423-25-4) + 3-tropanol (120-29-6)

Guidance literature:

With sodium thiophenolate; In acetonitrile; butanone; Heating;

Reference yield:

3-oxo-8-propyl-8-aza-bicyclo[3.2.1]octane-2,4-dicarboxylic acid → endo-8-(1-methylethyl)-8-azabicyclo<3.2.1>octan-3-ol (3423-25-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 6 M HCl / 1 h / 70 °C

2: Brugmansia candida x aurea / Enzymatic reaction

With hydrogenchloride; Brugmansia candida x aurea; 1: Decarboxylation / 2: Reduction;

DOI:10.1016/S0031-9422(99)00292-7

Reference yield:

8-aza-8-isopropyl-bicyclo<3.2.1>octan-3-one (3423-28-7) → exo-8-(1-methylethyl)-8-azabicyclo<3.2.1>octan-3-ol (3423-23-2) + endo-8-(1-methylethyl)-8-azabicyclo<3.2.1>octan-3-ol (3423-25-4)

Guidance literature:

With di-μ-chlorobis(norbornadiene)dirhodium(I); tributylphosphine; hydrogen; In methanol; benzene; at 50 ℃; for 6h; Rate constant; also in the presence of Et₃N + PPh₃;

DOI:10.1016/S0022-328X(00)99332-X

upstream raw materials:

8-aza-8-isopropyl-bicyclo<3.2.1>octan-3-one

(1R,3R,5S)-3-Hydroxy-8-isopropyl-8-methyl-8-azonia-bicyclo[3.2.1]octane; iodide

Downstream raw materials:

endo-8-(1-methylethy)-8-azabicyclo<3.2.1>oct-3-yl 2-phenyl-2-cyclohexene-1-carboxylate

(2-Phenyl-cyclohex-1-enyl)-acetic acid (1R,3R,5S)-8-isopropyl-8-aza-bicyclo[3.2.1]oct-3-yl ester

3-hydroxy-8-isopropyl-8-methyl-8-azonia-bicyclo[3.2.1]octane; bromide

(1R,3R,5S)-3'-hydroxy-2'-phenylpropionic acid 8-isopropyl-8-azabicyclo[3.2.1]oct-3-yl ester