Steric control of the asymmetric synthesis of N-substitued 2-methyl-4-piperidones

Grishina, G. V.; Potapov, V. M.; Abdulganeeva, S. A.; Korchagina, Elena

doi:10.1007/bf00842959

Cited by 2 publications

(4 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“… a Black compounds are those common to a majority of the synthetic routes. Specific compounds in orange, One Pot, Method 1; blue, Siegfried, Methods 2, 4, 6; green, Valdez, Method 3, 5; purple, N -methyl-4-piperidinone route, , Method 6. Methods 4, 5, and 6 are hybrid routes exploiting certain parts of the Valdez and Siegfried syntheses.…”

Section: Methodsmentioning

confidence: 99%

“…Method 5 is the complement to Method 4, using Siegfried NPP to generate fentanyl via the Valdez route (“Siegfried → Valdez”). Method 6 is the only route that uses N -methylpiperidone to generate NPP (“Alt NPP → Siegfried”). , The reaction then uses the Siegfried synthesis to form fentanyl.…”

Section: Methodsmentioning

confidence: 99%

“…Fentanyl Synthesis Summary a a Black compounds are those common to a majority of the synthetic routes. Specific compounds in orange, One Pot, 12 Method 1; blue, Siegfried, 14 Methods 2, 4, 6; green, Valdez, 13 Method 3, 5; purple, N-methyl-4-piperidinone route, 18,19 the published routes, all synthetic methods successfully yielded fentanyl with a range of purities. Because of the nature of the routes, complete synthetic details are not given in the present work, though they may be found in the literature cited.…”

mentioning

confidence: 99%

“…Method 6 is the only route that uses N-methylpiperidone to generate NPP ("Alt NPP → Siegfried"). 18,19 The reaction then uses the Siegfried synthesis to form fentanyl.…”

mentioning

confidence: 99%

See 3 more Smart Citations

Chemical Attribution of Fentanyl Using Multivariate Statistical Analysis of Orthogonal Mass Spectral Data

et al. 2016

View full text Add to dashboard Cite

Attribution of the origin of an illicit drug relies on identification of compounds indicative of its clandestine production and is a key component of many modern forensic investigations. The results of these studies can yield detailed information on method of manufacture, starting material source, and final product, all critical forensic evidence. In the present work, chemical attribution signatures (CAS) associated with the synthesis of the analgesic fentanyl, N-(1-phenylethylpiperidin-4-yl)-N-phenylpropanamide, were investigated. Six synthesis methods, all previously published fentanyl synthetic routes or hybrid versions thereof, were studied in an effort to identify and classify route-specific signatures. A total of 160 distinct compounds and inorganic species were identified using gas and liquid chromatographies combined with mass spectrometric methods (gas chromatography/mass spectrometry (GC/MS) and liquid chromatography-tandem mass spectrometry-time of-flight (LC-MS/MS-TOF)) in conjunction with inductively coupled plasma mass spectrometry (ICPMS). The complexity of the resultant data matrix urged the use of multivariate statistical analysis. Using partial least-squares-discriminant analysis (PLS-DA), 87 route-specific CAS were classified and a statistical model capable of predicting the method of fentanyl synthesis was validated and tested against CAS profiles from crude fentanyl products deposited and later extracted from two operationally relevant surfaces: stainless steel and vinyl tile. This work provides the most detailed fentanyl CAS investigation to date by using orthogonal mass spectral data to identify CAS of forensic significance for illicit drug detection, profiling, and attribution.

show abstract

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

“…Method 6 is the only route that uses N-methylpiperidone to generate NPP ("Alt NPP → Siegfried"). 18,19 The reaction then uses the Siegfried synthesis to form fentanyl.…”

mentioning

confidence: 99%

See 2 more Smart Citations

Chemical Attribution of Fentanyl Using Multivariate Statistical Analysis of Orthogonal Mass Spectral Data

et al. 2016

View full text Add to dashboard Cite

show abstract

Stereoselective Synthesis of [5‐[4,4,4,4′,4′,4′‐Hexafluoro‐N‐(2‐hydroxyethoxy)‐D‐valine]]‐ and [5‐[4,4,4,4′,4′,4′‐Hexafluoro‐N‐(2‐hydroxyethoxy)‐L‐valine]cyclosporin A

Eberle

Keese

2010

Helvetica Chimica Acta

View full text Add to dashboard Cite

Addition of various amines to the 3,3‐bis(trifluoromethyl)acrylamides 10a and 10b gave the tripeptides 11a–11f, mostly as mixtures of epimers (Scheme 3). The crystalline tripeptide 11f2 was found to be the N‐terminal (2‐hydroxyethoxy)‐substituted (R,S,S)‐ester HOCH2CH2O‐D‐Val(F6)‐MeLeu‐Ala‐OtBu by X‐ray crystallography. The C‐terminal‐protected tripeptide 11f2 was condensed with the N‐terminus octapeptide 2b to the depsipeptide 12a which was thermally rearranged to the undecapeptide 13a (Scheme 4). The condensation of the epimeric tripeptide 11f1 with the octapeptide 2b gave the undecapeptide 13b directly. The undecapeptides 13a and 13b were fully deprotected and cyclized to the [5‐[4,4,4,4′,4′,4′‐hexafluoro‐N‐(2‐hydroxyethoxy)‐D‐valine]]‐ and [5‐[4,4,4,4′,4′,4′‐hexafluoro‐N‐(2‐hydroxyethoxy)‐L‐valine]]cyclosporins 14a and 14b, respectively (Scheme 5). Rate differences observed for the thermal rearrangements of 12a to 13a and of 12b to 13b are discussed.

show abstract

Steric control of the asymmetric synthesis of N-substitued 2-methyl-4-piperidones

Cited by 2 publications

References 4 publications

Chemical Attribution of Fentanyl Using Multivariate Statistical Analysis of Orthogonal Mass Spectral Data

Chemical Attribution of Fentanyl Using Multivariate Statistical Analysis of Orthogonal Mass Spectral Data

Stereoselective Synthesis of [5‐[4,4,4,4′,4′,4′‐Hexafluoro‐N‐(2‐hydroxyethoxy)‐D‐valine]]‐ and [5‐[4,4,4,4′,4′,4′‐Hexafluoro‐N‐(2‐hydroxyethoxy)‐L‐valine]cyclosporin A

Contact Info

Product

Resources

About