Reductive <i>N</i>‐alkylation of secondary amines with [2‐<sup>11</sup>C]acetone

Meij, M. van der; Carruthers, Nicholas I.; Herscheid, J. D. M.; Jablonowski, Jill A.; Leysen, Josée E.; Windhorst, Albert D.

doi:10.1002/jlcr.740

Cited by 16 publications

(12 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[31][32][33] The hypothesis that the formation of tertiary alcohols (7) from [ 11 C]CO 2 is a kinetically controlled reaction of still unhydrolyzed organolithium reagent with newly formed ketone ( [2-11 C]acetone) during the hydrolysis step, was consistent with the observation that the quantity of 7 could be controlled by changing the amount of methyl lithium (MeLi). 33 The results of the present study showed that the formation of 7 compared to [2-11 C]acetone indeed was increased by using high(er) amounts of MeLi and omitting the destruction of its excess before hydrolysis of lithium diolate.…”

Section: Resultssupporting

confidence: 63%

Radiosynthesis of [¹¹C]docetaxel

Tilburg

Franssen

Hoeven

et al. 2004

Labelled Comp Radiopharmac

View full text Add to dashboard Cite

show abstract

Section: Resultssupporting

confidence: 63%

Radiosynthesis of [¹¹C]docetaxel

Tilburg

Franssen

Hoeven

et al. 2004

Labelled Comp Radiopharmac

View full text Add to dashboard Cite

show abstract

“…3 [ 11 C]Acetone has itself been utilised as a useful labelling intermediate in 11 C-chemistry. [44][45][46] Grignard and organolithium reagents are often used in 11 C-chemistry due to their great reactivity as nucleophiles for [ 11 C]CO 2 . However, as a consequence of their reactivity, these reagents do not have wide functional group compatibility and readily react with atmospheric CO 2 lowering the molar activity (A m ) of the final 11 Ctracer.…”

Section: Direct 11 C-carboxylationmentioning

confidence: 99%

Recent progress in [¹¹C]carbon dioxide ([¹¹C]CO₂) and [¹¹C]carbon monoxide ([¹¹C]CO) chemistry

Taddei

Gee

2018

Labelled Comp Radiopharmac

View full text Add to dashboard Cite

[ 11 C]Carbon dioxide ([ 11 C]CO 2 ) and [ 11 C]carbon monoxide ([ 11 C]CO) are 2 attractive precursors for labelling the carbonyl position (C═O) in a vast range of functionalised molecules (eg, ureas, amides, and carboxylic acids). The development of radiosynthetic methods to produce functionalised 11 C‐labelled compounds is required to enhance the radiotracers available for positron emission tomography, molecular, and medical imaging applications. Following a brief summary of secondary 11 C‐precursor production and uses, the review focuses on recent progress with direct 11 C‐carboxylation routes with [ 11 C]CO 2 and 11 C‐carbonylation with [ 11 C]CO. Novel approaches to generate [ 11 C]CO using CO‐releasing molecules (CO‐RMs), such as silacarboxylic acids and disilanes, applied to radiochemistry are described and compared with standard [ 11 C]CO production methods. These innovative [ 11 C]CO synthesis strategies represent efficient and reliable [ 11 C]CO production processes, enabling the widespread use of [ 11 C]CO chemistry within the wider radiochemistry community.

show abstract

“…One example of reductive amination of [2-11 C]acetone with a secondary amine has been described. In that aim, a fully automated synthesis of [2-11 C]acetone and the following reductive alkylation of 1-phenylpiperazine afforded the [ 11 C]-isopropyl-4phenylpiperazine ([ 11 C]iPPP) in 72% radiochemical yield (decay corrected) [248] (Fig. 72).…”

Section: Reductive Aminationsmentioning

confidence: 99%

State of Art in 11C Labelled Radiotracers Synthesis

Allard

Fouquet

James

et al. 2008

CMC

View full text Add to dashboard Cite

Positron Emission Tomography has become a powerful scientific and clinical tool probing biochemical processes in the human body. Their clinical applications have proven to be vital in the evaluation and diagnosis of diseases. This is due, in large part, to advances in instrumentation and synthetic chemistry. Carbon-11 is a valuable radionuclide in PET as it virtually permits the synthesis of radiolabelled versions of any compound of interest. The syntheses with carbon-11 present several features: limited number of labelled precursors, sub-micromolar amounts of the starting materials, and a need for the introduction of the radioisotope as late as possible in the synthesis. All of these reasons have restricted complex radiosyntheses. The short half-life of carbon-11 (20.4 min) requires the rapid preparation and purification of carbon-11 labelled molecules. Those have to be carried out immediately before use from cyclotron produced precursors ([11C]CO2, [11C]CO, [11C]CH4) or reagents rapidly prepared from them ([11C]CH3I, [11C]COCl2, [11C]HCN). As a consequence carbon-11 has been underused compared to fluorine-18. However, because of the increasing molecular complexity and diversity of biologically active compounds, there is a need for new methodologies giving access in short time and high yield to radioactive (11)C-probes. The aim of this review is to emphasize the methodologies used in this field and to give a comprehensive overview of the numerous advances, which occurred over the past decade. In addition, for each labelling technique or reaction reported, a special attention has been brought to classify the applications in function of the targeted medical domain.

show abstract

Reductive N‐alkylation of secondary amines with [2‐¹¹C]acetone

Cited by 16 publications

References 18 publications

Radiosynthesis of [¹¹C]docetaxel

Radiosynthesis of [¹¹C]docetaxel

Recent progress in [¹¹C]carbon dioxide ([¹¹C]CO₂) and [¹¹C]carbon monoxide ([¹¹C]CO) chemistry

State of Art in 11C Labelled Radiotracers Synthesis

Contact Info

Product

Resources

About

Reductive N‐alkylation of secondary amines with [2‐11C]acetone

Cited by 16 publications

References 18 publications

Radiosynthesis of [11C]docetaxel

Radiosynthesis of [11C]docetaxel

Recent progress in [11C]carbon dioxide ([11C]CO2) and [11C]carbon monoxide ([11C]CO) chemistry

State of Art in 11C Labelled Radiotracers Synthesis

Contact Info

Product

Resources

About

Reductive N‐alkylation of secondary amines with [2‐¹¹C]acetone

Radiosynthesis of [¹¹C]docetaxel

Radiosynthesis of [¹¹C]docetaxel

Recent progress in [¹¹C]carbon dioxide ([¹¹C]CO₂) and [¹¹C]carbon monoxide ([¹¹C]CO) chemistry