7123-92-4

Usage

Uses

Used in Chemical Synthesis:
Norpseudopelleterine-N-oxyl is used as an oxidant for the aerobic oxidation of alcohols and amines at room temperature and ambient pressure. Its application in this field is due to its ability to facilitate the conversion of these compounds into their corresponding carbonyl derivatives, which are essential intermediates in the synthesis of various pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Research Laboratories:
Norpseudopelleterine-N-oxyl is used as a convenient benchtop stable solid in research laboratories. Its stability and ease of handling make it an attractive choice for chemists working on the development of new synthetic methods and exploring the reactivity of various substrates with this oxidant.

InChI:InChI=1/C8H12NO2/c10-8-4-6-2-1-3-7(5-8)9(6)11/h6-7H,1-5H2

Synthetic route

9-azabicyclo[3.3.1]nonan-3-one (4390-39-0) → 9-oxyl-9-azabicyclo<3.3.1>nonan-3-one (7123-92-4)

Conditions	Yield
With sodium tungstate; dihydrogen peroxide
With sodium tungstate (VI) dihydrate; urea hydrogen peroxide adduct In water at 0 - 10℃; for 2h;	34.2 g

Glutaraldehyde (111-30-8) → 9-oxyl-9-azabicyclo<3.3.1>nonan-3-one (7123-92-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid; sodium acetate / water / 43 h / 0 - 30 °C / Darkness 2: hydrogen; palladium 10% on activated carbon / methanol / 27 h / 40 - 50 °C / 2068.65 - 2585.81 Torr 3: sodium tungstate (VI) dihydrate; urea hydrogen peroxide adduct / water / 2 h / 0 - 10 °C View Scheme

9-oxyl-9-azabicyclo<3.3.1>nonan-3-one (7123-92-4) + allyl (2-(1H-indol-3-yl)ethyl)carbamate (1548408-69-0) → C22H27N3O4

Conditions	Yield
With acetic acid; sodium nitrite In water; acetonitrile at 20℃; for 0.5h;

9-oxyl-9-azabicyclo<3.3.1>nonan-3-one (7123-92-4) + Fmoc-Gly-Ser-Asn-Trp-Gly-OH → C45H52N8O13 + C45H50N8O12

Conditions	Yield
With acetic acid; sodium nitrite In water; acetonitrile at 20℃; for 0.5h; Overall yield = 95 %Chromat.;

9-oxyl-9-azabicyclo<3.3.1>nonan-3-one (7123-92-4) + Fmoc-Gly-Lys-Asn-Trp-Gly-OH → C48H59N9O12 + C48H57N9O11

Conditions	Yield
With acetic acid; sodium nitrite In water; acetonitrile at 20℃; for 0.5h; Overall yield = 95 %Chromat.;

9-oxyl-9-azabicyclo<3.3.1>nonan-3-one (7123-92-4) + C51H48N10O12 → C59H61N11O15 + C59H59N11O14

Conditions	Yield
With acetic acid; sodium nitrite In water; acetonitrile at 20℃; for 0.5h;

Upstream product

• 111-30-8 Glutaraldehyde 
• 4390-39-0 9-azabicyclo[3.3.1]nonan-3-one 

Relevant academic research and scientific papers

Electron Loss from 1,3,3-Trimethyl-2-azabicyclooctane Derivatives. Is ? Coupling Thermodynamically Important?

The ease of one-electron oxidation is compared for ? coupled and non-?-coupled γ-oxopiperidine nitroxides and their saturated analogues (CO -> CH2).For the non-?-coupled pair, 1,3,3-trimethyl-2-oxyl-2-azabicyclooctan-5-one (9) has IPv = 7.29 eV, Eo' = 0.73 V and its CO -> CH2 analogue 11 IPv = 6.88, Eo' = 0.52 V.The ?-coupled pair 9-oxyl-9-azabicyclononan-3-one (12) has IPv = 7.78 eV, Eo' = 0.83 V and its CO -> CH2 analogue 13 IPv = 7.39 eV, Eo' = 0.58 V.Replacement of CO by CH2 in the non-?-coupled example has as large an effectof IPv and only a 13percent smaller effect on Eo' than in the ?-coupled example, making it appear that a ?-coupled transmission of positive charge from the nitrogen to the carbonyl in the radical cation is unimportant.

Preparation of ABNO on Scale and Analysis by Quantitative Paramagnetic NMR

A practical, safe, and scalable synthesis of the stable nitro-oxide radical catalyst ABNO was developed. This process is chromatography-free and avoids the Wolff-Kishner reduction. 1H NMR data for this paramagnetic compound were obtained that allowed an assessment of its chemical purity. Impact sensitivity test data for solid ABNO are also reported.