endo-(±)-8-aza-8-isopropylbicyclo[3.2.1]oct-3-yl (hydroxymethyl)phenylacetate

Base Information

• Chemical Name: endo-(±)-8-aza-8-isopropylbicyclo[3.2.1]oct-3-yl (hydroxymethyl)phenylacetate
• CAS No.: 22235-81-0
• Molecular Formula: C19H27NO3
• Molecular Weight: 317.428
• Hs Code.: 2933990090
• Mol file: 22235-81-0.mol

Synonyms:(8-propan-2-yl-8-azabicyclo[3.2.1]octan-3-yl) 3-hydroxy-2-phenylpropanoate;

Chemical Property of endo-(±)-8-aza-8-isopropylbicyclo[3.2.1]oct-3-yl (hydroxymethyl)phenylacetate

Chemical Property:

• Vapor Pressure: 7.72E-09mmHg at 25°C
• Melting Point: 112-114°C
• Boiling Point: 448.8°C at 760 mmHg
• PKA: 14.12±0.10(Predicted)
• Flash Point: 225.2°C
• PSA: 49.77000
• Density: 1.15g/cm³
• LogP: 2.64740
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

99.9% ^*data from raw suppliers

N-IsopropylNoratropine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-Isopropyl Noratropine is a Noratropine derivative, an intermediate in the production of Ipratropium.

Technology Process of endo-(±)-8-aza-8-isopropylbicyclo[3.2.1]oct-3-yl (hydroxymethyl)phenylacetate

There total 8 articles about endo-(±)-8-aza-8-isopropylbicyclo[3.2.1]oct-3-yl (hydroxymethyl)phenylacetate 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: 64.6%

α-formylphenylacetic acid N-isopropylnortropine ester → (1R,3R,5S)-3'-hydroxy-2'-phenylpropionic acid 8-isopropyl-8-azabicyclo[3.2.1]oct-3-yl ester (22235-81-0,183626-76-8)

Guidance literature:

With potassium borohydride; In chloroform; water; at 0 - 10 ℃; for 4h; Reagent/catalyst; Temperature; Solvent;

Reference yield: 62.0%

acetone (67-64-1) + Noratropine (16839-98-8) → (1R,3R,5S)-3'-hydroxy-2'-phenylpropionic acid 8-isopropyl-8-azabicyclo[3.2.1]oct-3-yl ester (22235-81-0,183626-76-8)

Guidance literature:

With sodium cyanoborohydride; acetic acid; In methanol; at 20 ℃; for 4.5h; pH=7;

DOI:10.1071/CH05303

Reference yield:

endo-8-(1-methylethyl)-8-azabicyclo<3.2.1>octan-3-ol (3423-25-4) → (1R,3R,5S)-3'-hydroxy-2'-phenylpropionic acid 8-isopropyl-8-azabicyclo[3.2.1]oct-3-yl ester (22235-81-0,183626-76-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 4 h / 85 °C

2: 0.89 g / hydrochloric acid / CHCl₃ / 18 h

With hydrogenchloride; In chloroform;

DOI:10.1080/00397910601039119

upstream raw materials:

acetone

Noratropine

Atropine

3-acetoxy-2-phenyl-propionyl chloride

Refernces

• 1、 -. "Preparation method of ipratropium bromide". . . Retrieved 2017/06/14.
• 2、 Issa, Fatiah,Kassiou, Michael,Chan, Hak-Kim,McLeod, Malcolm D.. "Synthesis and radiolabelling of ipratropium and tiotropium for use as PET ligands in the study of inhaled drug deposition". . p. 53 - 58. Retrieved 2007/10/03.