(9S)- 3,10-Didehydro-10,11-dihydro-6'-methoxycinchonan-9-ol Acetate

Base Information

• Chemical Name: (9S)- 3,10-Didehydro-10,11-dihydro-6'-methoxycinchonan-9-ol Acetate
• CAS No.: 139239-49-9
• Molecular Formula: C₂₂H₂₆N₂O₃
• Molecular Weight: 366.46
• Mol file: 139239-49-9.mol

Synonyms:9-Acetyl Apoquinidine Methyl Ether;

Chemical Property of (9S)- 3,10-Didehydro-10,11-dihydro-6'-methoxycinchonan-9-ol Acetate

Chemical Property:

• Appearance/Colour: yellow solid
• Melting Point: 178-180 °C
• PSA: 51.66000
• LogP: 3.82600
• Storage Temp.: Refrigerator
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

98%min ^*data from raw suppliers

9-AcetylApoquinidineMethylEther ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: A synthetic quinidine derivative

Technology Process of (9S)- 3,10-Didehydro-10,11-dihydro-6'-methoxycinchonan-9-ol Acetate

There total 4 articles about (9S)- 3,10-Didehydro-10,11-dihydro-6'-methoxycinchonan-9-ol Acetate 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: 82.0%

acetic anhydride (108-24-7) + (S)-((2R)-5-ethylidene-1-azabicyclo[2.2.2]oct-2-yl)-(6-methoxy-quinoline-4-yl)-methanol (139237-97-1,697260-51-8) → apoquinidine methyl ether 9-acetate (139239-49-9)

Guidance literature:

With pyridine; at 25 ℃; for 16h;

DOI:10.1039/P19910003017

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) → apoquinidine methyl ether 9-acetate (139239-49-9)

Guidance literature:

Multi-step reaction with 3 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

With pyridine; hydrogen bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide;

DOI:10.1039/P19910003017

Reference yield:

α-10-bromodihydroquinidine (53922-99-9,55903-76-9,60723-41-3,60723-42-4,65026-55-3,105662-27-9) → apoquinidine methyl ether 9-acetate (139239-49-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / DBU / dimethylsulfoxide / 2 h / 85 - 90 °C

2: 82 percent / pyridine / 16 h / 25 °C

With pyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide;

DOI:10.1039/P19910003017

upstream raw materials:

acetic anhydride

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

(+)-quinidine

α-10-bromodihydroquinidine

Downstream raw materials:

3-hydroxyquinidine

(3R)-3-hydroxyquinidine

(3S)-3-hydroxyquinidine 9-benzoate

(8R,9S)-6'-methoxy-3-oxoruban-9-yl acetate

Refernces