Structure elucidation via stereoselective synthesis of the acetate center of 1-Azabicyclo[2.2.2]oct-3-yl {alpha}-hydroxy-{alpha}(1-iodo-1-propen-3-yl)-{alpha}-phenylacetate (IQNP). A high affinity muscarinic imaging agent for SPECT

Journal Article · Thu Nov 14 23:00:00 EST 1996 · Journal of Organic Chemistry

DOI:https://doi.org/10.1021/jo961033t· OSTI ID:494235

McPherson, D W; Knapp, Jr, F F ^[1]

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1. Oak Ridge National Lab., TN (United States)

A facile stereoselective synthesis of {alpha}-hydroxy-{alpha}-phenyl-{alpha}-(1-propyn-3-yl)acetic acid in high enantiomeric excess has been developed and allows determination of the (R/S) conformation at this center. In addition, comparison of the specific rotation, HPLC, and NMR data of (E)-(R,R)-and (E)-(R,S)-IQNP to those prepared by a classical resolution of the acetate moiety allows the assignment of (E)-(R,R)-IQNP as the isomer demonstrating binding to the M{sub 1} mAChR subtype and (Z)-(R,R)-IQNP as the isomer binding to both the M{sub 1} and M{sub 2} mAChR subtypes.

• DOE Contract Number: AC05-96OR22464
• OSTI ID: 494235
• Journal Information: Journal of Organic Chemistry, Journal Name: Journal of Organic Chemistry Journal Issue: 23 Vol. 61; ISSN JOCEAH; ISSN 0022-3263
• Country of Publication: United States
• Language: English

Related Subjects

40 CHEMISTRY
55 BIOLOGY AND MEDICINE
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CHEMICAL PREPARATION
LIQUID COLUMN CHROMATOGRAPHY
NUCLEAR MAGNETIC RESONANCE
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
SINGLE PHOTON EMISSION COMPUTED TOMOGRAPHY
STEREOCHEMISTRY
STRUCTURAL CHEMICAL ANALYSIS