Synthesis and Physiological Action of Alpha Substituted N-Methylpyrrolidines

Craig, Lyman C.

doi:10.1021/ja01333a052

Cited by 19 publications

(3 citation statements)

References 4 publications

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“…While compounds ( 1a , 1b , 1c ) were commercially available, N ‐methyl‐2‐phenyl‐pyrrolidine ( 1d ) was synthesized according to Craig by reaction of N ‐methyl‐α‐pyrrolidone with phenylmagnesium bromide, and subsequent reduction of the resulting crude product with magnesium turnings and hydrochloric acid.…”

Section: Resultsmentioning

confidence: 99%

Quantification of the nucleophilic reactivity of nicotine

Byrne

Kobayashi

Breugst

et al. 2016

J of Physical Organic Chem

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Rate and equilibrium constants of the reactions of nicotine and structurally related compounds with benzhydrylium ions have been determined UV-Vis spectroscopically using stopped-flow and laser-flash techniques. The pyridine nitrogen of nicotine was identified as the site of thermodynamically and kinetically controlled attack. Quantum chemical calculations showed that the introduction of a pyrid-3-yl moiety into the 2-position of N-methylpyrrolidine (to give nicotine) reduces the Lewis basicity of the pyrrolidine ring by 24 kJ mol À1 , whereas the analogous introduction of a phenyl ring decreases this quantity by only 11 kJ mol À1 . Scheme 3. Reactions of nicotine (1a) with benzhydrylium ions 2h and 2q to give N-diarylmethylpyridinium salts (3h and 3q) Scheme 4. Reactions of (mfa) 2 CH + À BF 4 (2h) with (a) 3-methylpyridine (1b) to give pyridinium 5b and (b) N-methylpyrrolidine (1c) to give Ndiarylmethyl-N-methylpyrrolidinium salt 5c NUCLEOPHILIC REACTIVITY OF NICOTINE a The quoted values of N and s N for 1c were reported in ref. 8. NUCLEOPHILIC REACTIVITY OF NICOTINE

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Section: Resultsmentioning

confidence: 99%

Quantification of the nucleophilic reactivity of nicotine

Byrne

Kobayashi

Breugst

et al. 2016

J of Physical Organic Chem

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“…(R)-1-Methyl-2-(n-butyl)pyrrolidine, 25a, 7 was prepared from 22a (R = butyl) in 66% yield as a colorless oil after flash chromatography:…”

Section: S7mentioning

confidence: 99%

“…[α] D = + 23.5° (c = 0.4, CHCl 3). This compound is known in the literature in racemic form,7 but no rotation or NMR data has previously been reported. (R)-1-Methyl-2-(allyl)pyrrolidine, 25d,10 was prepared from 22d (R = allyl) in 62% yield as an oil after flash chromatography: [α] D = + 12.5° (c = 0.2, CHCl 3 ).…”

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confidence: 98%

Conversion of Five‐, Six‐, and Seven‐Membered Lactams to Racemic or Scalemic 2‐Substituted Heterocycles by Amidoalkylation.

et al. 2005

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Pyridine derivatives R 0380Conversion of Five-, Six-, and Seven-Membered Lactams to Racemic or Scalemic 2-Substituted Heterocycles by Amidoalkylation. -The process offers an efficient route to racemic and enantiopure 2-substituted pyrrolidines, piperidines, and azepanes. -(MADAN, S.; MILANO, P.; EDDINGS, D. B.; GAWLEY*, R. E.; J. Org. Chem. 70 (2005) 8, 3066-3071; Dep. Chem. Biochem., Univ. Ark., Fayetteville, AR 72701, USA; Eng.) -Jannicke 37-138

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Über die Alkaloide von Heliotropium Lasiocarpum, VI. Mitteil.: Synthese einiger Pyrrolidin‐Derivate

Menschikoff¹,

Schdanowitsch²

1936

Ber. dtsch. Chem. Ges. A/B

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M e 18.g c h i k o f f , S c h d a n ow i t s c h. 1799 322. G. Menschikoff und J e k a t e r i n a Schdanowitsch: Ober die Alkaloide von Heliotropium Lasiocarpum, VI. Mitteil.: Synthese einig er P yrrolidin-D eriva te . [AUS d. Alkaloid-Abteil. d. Staatl. Chem.-pharmazeut. Porschungs-Instituts, Moskau').] (Eingegangen am 22. Juni 1936.) Wie bereits von dem einen von uns mitgeteilt wurde,), bildet sich bei der katalytischen Dehydriemg des Dihydro-des-N-methyl-heliotridans eine Base, die zur Pyrrol-Reihe gehort . Dadurch erweist sich das Dihydro-h-N-methylheliotridan selbst als zur Pyrrolidin-Reihe zugehorig. Urn diese Korper mit Pyrrolidin-Derivaten bekannter Struktur (mit 9 Kohlenstoffatomen) zu vergleichen, stellten wir nach einem neuen Verfahren, das keinerlei Zweifel uber die Konstitution der zu erhaltenden Basen zuldt, das 2 -~B u t y l -und das 2-Isobutyl-pyrrolidin sowie deren N-Methyl-Derivate dar. A l s Ausgangsmaterial fur die Synthese des 2-Is o b u t y 1p y r r ol id i ns dienten 1 -J od -3met hox ypr op ans) und IS Ob u t y 1c y a ni d (fur 2-n-B u t y 1-p y r r oli din entsprechend n -B u t y 1c y ani d), aus welchen mittels der G r ig n a r dschen Reaktion 2 -Met h y 1 -7met h o XYhep t anon, (CH,),CH. CH, . CO. [CHJ, .O. CHs, gewonnen wurde. Diewurde ins Oxim verwandelt und mit Natrium in absol. Butylalkohol zum 2 -Met h y 1 -4 -am i n 0-7 -met h o x yhe p t a n reduziert, das beim Erhitzen mit Bromwasserstoffsiiure in guter Ausbeute 2-I sobut y 1 -p y r roli di n gab : CH,--CH2 CHsY!H. CH, . 6H . NH, AH,. 0.

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Synthesis and Physiological Action of Alpha Substituted N-Methylpyrrolidines

Cited by 19 publications

References 4 publications

Quantification of the nucleophilic reactivity of nicotine

Quantification of the nucleophilic reactivity of nicotine

Conversion of Five‐, Six‐, and Seven‐Membered Lactams to Racemic or Scalemic 2‐Substituted Heterocycles by Amidoalkylation.

Über die Alkaloide von Heliotropium Lasiocarpum, VI. Mitteil.: Synthese einiger Pyrrolidin‐Derivate

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