Evidence map›Paper›PMID 30906182›Full record

ArticleOrganic process research & development2018

Continuous Platform to Generate Nitroalkanes On-Demand (in situ) using Peracetic Acid-Mediated Oxidation in a PFA Pipes-in-Series Reactor.

Sergey V Tsukanov, Martin D Johnson, Scott A May, Stanley P Kolis, Matthew H Yates, Jeffrey N Johnston

Abstract read
In one paragraph

Article in Organic process research & development, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.

0numbers the graph read from it
0cells of the map it votes in
3citing papers in PubMed
0.8field-weighted citation impact, top 30% of its field
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

3 citing papers in PubMed, 18 citations in OpenAlex.

  1. Review
  2. Article
  3. Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

6 authors at 2 institutions in 1 country.

Sergey V TsukanovSmall Molecule Design and Development, Eli Lilly and Company, Indianapolis, Indiana 46285, Unites States.
Martin D JohnsonSmall Molecule Design and Development, Eli Lilly and Company, Indianapolis, Indiana 46285, Unites States.
Scott A MaySmall Molecule Design and Development, Eli Lilly and Company, Indianapolis, Indiana 46285, Unites States.
Stanley P KolisSmall Molecule Design and Development, Eli Lilly and Company, Indianapolis, Indiana 46285, Unites States.
Matthew H YatesSmall Molecule Design and Development, Eli Lilly and Company, Indianapolis, Indiana 46285, Unites States.
Jeffrey N JohnstonDepartment of Chemistry and Vanderbilt Institute of Chemical Biology, Vanderbilt University, Nashville, Tennessee 37235, United States.
Eli Lilly (United States) · USVanderbilt University · US

Funding

New Stereoselective Reactions for Chiral Amine SynthesisR01GM084333 · NIGMS · VANDERBILT UNIVERSITY · PI JOHNSTON, JEFFREY NICHOLAS · 2009 to 2017
$2.2M
NIGMS NIH HHS R01 GM084333
6 · The paper itself

Abstract

The synthetic utility of the aza-Henry reaction can be diminished on scale by potential hazards associated with the use of peracid to prepare nitroalkane substrates, and the nitroalkanes themselves. In response, a continuous and scalable chemistry platform to prepare aliphatic nitroalkanes on-demand is reported, using the oxidation of oximes with peracetic acid and direct reaction of the nitroalkane intermediate in an aza-Henry reaction. A uniquely designed pipes-in-series plug flow tube reactor addresses a range of process challenges including stability and safe handling of peroxides and nitroalkanes. The subsequent continuous extraction generates a solution of purified nitroalkane which can be directly used in the following enantioselective aza-Henry chemistry to furnish valuable chiral diamine precursors in high selectivity, thus, completely avoiding isolation of potentially unsafe low molecular weight nitroalkane intermediate. A continuous campaign (16 h) established that these conditions were effective in processing 100 g of the oxime and furnishing 1.4 L of nitroalkane solution.

Indexed as

continuous processingflow chemistrynitroalkaneperoxidepipes-in-series reactorsustainable or green chemistry

Identifiers

PMID30906182
PMCPMC6424520
OpenAlexW2883008348

What OpenQuestion holds

Textmetadata
LicenceTDM
Read underepoch 390

Registered trials

None linked

Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.