Two Scalable Syntheses of (S)-2-Methylazetidine

The Journal of Organic Chemistry
Matthew S DowlingAaron C Smith

Abstract

Two orthogonal routes for preparing (S)-2-methylazetidine as a bench stable, crystalline (R)-(-)-CSA salt are presented. One route features the in situ generation and cyclization of a 1,3-bis-triflate to form the azetidine ring, while the second route involves chemoselective reduction of N-Boc azetidine-2-carboxylic acid. Both sequences afford the desired product in good overall yields (61% and 49%) and high enantiomeric excess (>99% ee), avoid column chromatography, and are suitable for the large-scale production of this material.

References

Oct 25, 2001·The Journal of Organic Chemistry·Aiko NabeyaKenzi Hori
Nov 26, 2003·Drugs·Keri Wellington, Lesley J Scott
May 20, 2006·The Journal of Organic Chemistry·Dalian ZhaoGuy R Humphrey
Sep 26, 2006·The Journal of Organic Chemistry·Michael C Hillier, Cheng-yi Chen
Sep 11, 2008·Chemical Reviews·Alberto BrandiFranca M Cordero
Mar 18, 2010·Angewandte Chemie·David M Hodgson, Johannes Kloesges
Apr 7, 2010·The Journal of Immunology : Official Journal of the American Association of Immunologists·Jordan S FridmanKris Vaddi
Apr 27, 2012·Journal of Medicinal Chemistry·David J St Jean, Christopher Fotsch
Mar 8, 2013·ChemMedChem·Andreas F G GlawarGeorge W J Fleet
May 10, 2013·The Journal of Organic Chemistry·Arjun RaghuramanKevin Burgess
Sep 30, 2014·The New England Journal of Medicine·James LarkinAntoni Ribas

❮ Previous
Next ❯

Citations

Jul 23, 2016·The Journal of Organic Chemistry·Alpa K PancholiMichael Shipman
Nov 11, 2019·Nature Communications·Marc R BeckerCorinna S Schindler

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.