O-Desmethyl Quinidine

• CAS: 70877-75-7
• Catalog Number: ACM70877757
• Category: Main Products
• Molecular Weight: 310.39
• Molecular Formula: C19H22N2O2
• Synonyms: 6'-Hydroxycinchonine
• Melting Point: 149 - 152 °C
• Appearance: Solid

Case Study

O-Desmethyl Quinidine as a Chiral Organocatalyst for Asymmetric Synthesis of SV2A PET Tracer Precursors

Qin, Marong, et al. Chemical Communications 61.90 (2025): 17689-17692.

Positron emission tomography (PET) imaging of synaptic vesicle glycoprotein 2A (SV2A) enables non-invasive quantification of synaptic density, a key biomarker for neurodegenerative diseases. The 18F-labeled radiotracers SynVesT-1 and SynVesT-2 show superior imaging characteristics for the R-enantiomer, yet accessing enantiomerically pure precursors remains challenging. In this study, O-desmethyl quinidine was employed as a chiral organocatalyst to enable the first asymmetric synthesis of enantiomerically enriched boronic ester precursors for both radiotracers.
The synthetic strategy employed O-desmethyl quinidine-catalyzed asymmetric Michael addition as the key stereochemistry-defining step. Addition of 20 mol% DIPEA as a co-catalyst proved essential for achieving high enantioselectivity, improving the enantiomeric ratio from 82:18 to >99:1 for SynVesT-1 and from 90:10 to >99:1 for SynVesT-2. The resulting chiral butyrolactam intermediates were further elaborated to the target aryl boronic ester precursors via N-alkylation and Miyaura borylation.
Key Results: O-Desmethyl quinidine (10 mol%) with DIPEA (20 mol%) catalyzed asymmetric Michael addition of diethyl malonate to nitroalkenes with >99:1 enantiomeric ratio for both SynVesT-1 and SynVesT-2 precursors. The methodology enabled isolation of enantiopure aryl Bpin precursors in 46% yield (SynVesT-1) and comparable yields for SynVesT-2 after 5-step sequences. Automated copper-mediated 18F-fluorination of these precursors produced multi-GBq quantities of both radiotracers (1.9-2.8 GBq) with complete retention of stereochemical integrity (>99:1 e.r.).

Custom Q&A

What is the molecular formula of O-Desmethyl Quinidine?

The molecular formula of O-Desmethyl Quinidine is C19H22N2O2.

What are the synonyms for O-Desmethyl Quinidine?

The synonyms for O-Desmethyl Quinidine are Cupreidine, 70877-75-7, CINCHONAN-6',9-DIOL, (9S)-, and 4-((S)-Hydroxy((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methyl)quinolin-6-ol.

What is the molecular weight of O-Desmethyl Quinidine?

The molecular weight of O-Desmethyl Quinidine is 310.4 g/mol.

When was O-Desmethyl Quinidine created and modified?

O-Desmethyl Quinidine was created on October 26, 2006, and modified on October 21, 2023.

What is the IUPAC name of O-Desmethyl Quinidine?

The IUPAC name of O-Desmethyl Quinidine is 4-[(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-hydroxymethyl]quinolin-6-ol.

What is the InChI of O-Desmethyl Quinidine?

The InChI of O-Desmethyl Quinidine is InChI=1S/C19H22N2O2/c1-2-12-11-21-8-6-13(12)9-18(21)19(23)15-5-7-20-17-4-3-14(22)10-16(15)17/h2-5,7,10,12-13,18-19,22-23H,1,6,8-9,11H2/t12-,13-,18+,19-/m0/s1.

What is the InChIKey of O-Desmethyl Quinidine?

The InChIKey of O-Desmethyl Quinidine is VJFMSYZSFUWQPZ-WXPXUSHHSA-N.

What is the canonical SMILES of O-Desmethyl Quinidine?

The canonical SMILES of O-Desmethyl Quinidine is C=CC1CN2CCC1CC2C(C3=C4C=C(C=CC4=NC=C3)O)O.

What is the CAS number of O-Desmethyl Quinidine?

The CAS number of O-Desmethyl Quinidine is 70877-75-7.

What is the XLogP3 value of O-Desmethyl Quinidine?

The XLogP3 value of O-Desmethyl Quinidine is 2.6.

Synthetic Use

Upstream Synthesis Route 1

• 56-54-2

• 70877-75-7

Reference: [1]Current Patent Assignee: WILLIAM MARSH RICE UNIVERSITY - WO2017/180248, 2017, A1
Location in patent: Page/Page column 67; 68