9-Acetoxyrubanone

Base Information

• Chemical Name: 9-Acetoxyrubanone
• CAS No.: 60723-43-5
• Molecular Formula: C₂₀H₂₂N₂O₄
• Molecular Weight: 354.406
• Hs Code.: 2933990090
• Mol file: 60723-43-5.mol

Synonyms:(8R, 9S)-6'-Methoxy-3-oxoruban-9-yl Acetate;(8R,9S)-6-Methoxy-3-oxo-9-rubanol Acetate;(9S)-9-(Acetyloxy)-6'-methoxy-10,11-dinorcinchonan-3-one;6'-Methoxy-3-oxo-9-rubanol Acetate;9-Acetoxyrubanone;ICQ 9

Chemical Property of 9-Acetoxyrubanone

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 162-163°C
• Refractive Index: 1.625
• Boiling Point: 524.34°C at 760 mmHg
• Flash Point: 270.911°C
• PSA: 68.73000
• Density: 1.298g/cm³
• LogP: 2.44880
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

98%min ^*data from raw suppliers

9-AcetoxyRubanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: An intermediate for the preparation of (3S)-3-Hydroxy Quinidine

Technology Process of 9-Acetoxyrubanone

There total 6 articles about 9-Acetoxyrubanone 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: 86.0%

Acetic acid (S)-[(2R,4S)-5-hydroxy-5-(1-hydroxy-ethyl)-1-aza-bicyclo[2.2.2]oct-2-yl]-(6-methoxy-quinolin-4-yl)-methyl ester → (8R,9S)-6'-methoxy-3-oxoruban-9-yl acetate (60723-43-5)

Guidance literature:

With sodium periodate; acetic acid; for 0.25h; Ambient temperature;

Reference yield: 56.0%

Acetic acid (S)-[(2R,4S)-5-hydroxy-5-(1-hydroxy-ethyl)-1-aza-bicyclo[2.2.2]oct-2-yl]-(6-methoxy-quinolin-4-yl)-methyl ester → 6-methoxyquinoline-4-carbaldehyde (4363-94-4) + (8R,9S)-6'-methoxy-3-oxoruban-9-yl acetate (60723-43-5)

Guidance literature:

With sodium periodate; In diethyl ether; water; for 2h; Ambient temperature;

Reference yield:

(+)-quinidine (56-54-2,130-95-0,572-59-8,572-60-1,42151-59-7,47342-58-5,72402-50-7,72402-51-8,72402-52-9,72402-53-0,101143-86-6,101143-87-7,101143-88-8,146925-10-2) → (8R,9S)-6'-methoxy-3-oxoruban-9-yl acetate (60723-43-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 48percent aq. hydrobromic acid, HBr(g) / a.) 0 deg C, 1 h, b.) 25 deg C, 1 h

2: 79 percent / DBU / dimethylsulfoxide / 2 h / 85 - 90 °C

3: 82 percent / pyridine / 16 h / 25 °C

4: 1.) OsO₄, 2.) NaIO₄ / 1.) 80percent HOAc, 25 deg C, 3 h, 2.) 4 deg C, 16 h

With pyridine; sodium periodate; osmium(VIII) oxide; hydrogen bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide;

DOI:10.1039/P19910003017

upstream raw materials:

apoquinidine methyl ether 9-acetate

(+)-quinidine

(S)-((2R)-5-ethylidene-1-azabicyclo[2.2.2]oct-2-yl)-(6-methoxy-quinoline-4-yl)-methanol

α-10-bromodihydroquinidine

Downstream raw materials:

(3R)-3-hydroxyquinidine

3-hydroxyquinidine

(3S)-3-hydroxyquinidine 9-benzoate