23581-42-2

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 3457, 1956 DOI: 10.1021/ja01595a053

Upstream product

• 50-00-0 formaldehyd 
• 21938-23-8 5-Aminopentanal Diethyl Acetal 
• 105-50-0 diethyl 1,3-acetonedicarboxylate 
• 106051-13-2 hexahydrospiroisoxazolo<2,3-a>pyridine> 
• 87265-40-5 4-(5,5-Diethoxy-pentylamino)-butan-2-one 
• 109-06-8 α-picoline 
• 27132-81-6 2,4-dimethyl-penta-1,4-dien-3-one 
• 49552-70-7 4-(1,3-dioxolan-2-yl)butan-1-amine 
• 34418-91-2 2,3,4,5-tetrahydropyridine N-oxide 
• 337974-51-3 8-[(tert-butoxycarbonyl)amino]-1-[(4'-methylphenyl)sulfonyl]-1-nonen-3-one 
• 98202-45-0 ethyl (2E)-7-iodohept-2-enoate 
• 2739-98-2 ethyl 2-(pyridinyl-2)acetate 
• 2739-99-3 2-ethoxycarbonylmethylpiperidine 
• 24103-75-1 4-methoxy-2-methylpyridine 

Downstream Products

• 475301-86-1 3-methyldecahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocine 
• 475301-86-1 (1S,5R,11aR)-3-methyldecahydro-1H-1,5-methanopyrido[1,2-a]-[1,5]diazocine 
• 475301-86-1 (+)-sparteine surrogate 
• 99392-98-0 1,2,3,4,6,7,8,9-octahydro-2-<β-(3,4-dimethoxyphenethylamino)ethyl>-9aH-quinolizine 
• 99405-57-9 2-(3,4-dimethoxyphenethylcarbamoylmethyl)-1,2,3,4,6,7,8,9-octahydro-9aH-quinolizine 
• 98482-42-9 4-Acetylamino-5-chloro-2-methoxy-N-(2R,9aR)-octahydro-quinolizin-2-yl-benzamide 
• 98482-44-1 4-Acetylamino-5-chloro-2-methoxy-N-(2R,9aS)-octahydro-quinolizin-2-yl-benzamide 
• 98482-28-1 (2β,9aα)-4-amino-5-chloro-2-methoxy-N-(octahydro-2H-quinolizin-2-yl)benzamide 
• 98482-30-5 (2α,9aα)-4-amino-5-chloro-2-methoxy-N-(octahydro-2H-quinolizin-2-yl)benzamide 
• 67092-45-9 2-amino-quinolizidine 
• 4968-90-5 eq-quinolizidin-2-ylmethanol 
• 475301-86-1 (+)-sparteine surrogate 
• 475301-86-1 (-)-sparteine 
• 475301-86-1 11-methyl-7,11-diazatricyclo<7.3.1.0^2.7>tridecane 

Relevant academic research and scientific papers

Revisiting the sparteine surrogate: Development of a resolution route to the (-)-sparteine surrogate

The improved performance of the sparteine surrogate compared to sparteine in a range of applications has highlighted the need to develop an approach to the (-)-sparteine surrogate, previously inaccessible in gram-quantities. A multi-gram scale, chromatography-free synthesis of the racemic sparteine surrogate and its resolution via diastereomeric salt formation with (-)-O,O′-di-p-toluoyl-l-tartaric acid is reported. Resolution on a 10.0 mmol scale gave the diastereomeric salts in 33% yield from which (-)-sparteine surrogate of 937 er was generated. This work solves a key limitation: either enantiomer of the sparteine surrogate can now be readily accessed.

HISTAMINE H3 INVERSE AGONISTS AND ANTAGONISTS AND METHODS OF USE THEREOF

Provided herein are spiro-cyclic compounds, methods of synthesis, and methods of use thereof. The compounds provided herein are useful for the treatment, prevention, and/or management of various disorders, including, e.g., neurological disorders and metab

A two-step, formal [4 + 2] approach toward piperidin-4-ones via au catalysis

(Chemical Equation Presented) An efficient, formal [4 + 2] synthesis of synthetically valuable piperidin-4-ones from secondary amines in two steps has been achieved via a key gold catalysis without the purification of tertiary amine intermediates. This reaction is selective toward the less-substituted alkyl group and shows moderate to excellent diastereoselectivities. Its synthetic potential in alkaloid synthesis is demonstratedin a highly diastereoselective synthesis of (±)-cermizine C.

Synthesis of sparteine-like chiral diamines and evaluation in the enantioselective lithiation-substitution of N-(tert-butoxycarbonyl)-pyrrolidine

Three chiral diamines were synthesised and evaluated as sparteine surrogates in the lithiation-substitution of N-(tert-butoxycarbonyl)pyrrolidine. The synthesis and attempted resolution of sparteine-like diamines {(1S*, 2R*, 8R*)-10-methyl-6,10-diazatricyclo [6.3.1.02,6]dodecane and (1S*, 2R*, 9R*)-11-methyl-7,11-diazatricyclo[7.3.1.02,7]tridecane} (via inclusion complex formation) are reported. Unfortunately, it was only possible to resolve the diazatricyclo-[7.3.1.02,7] tridecane compound. An alternative route to (1R,2S,9S)-11-methyl-7,11-diazatricyclo[7.3.1.02.7]tridecane starting from the natural product, (-)-cytisine, is described. This simple three-step route furnished gram-quantities of a (+)-sparteine surrogate. X-ray crystallography of an intermediate in the route, (1R,5S,12S)-3-methoxycarbonyl-decahydro-1,5-methanopyrido [1,2-a][1,5]diazocin-8-one, enabled the stereochemistry of all of the tricyclic diamines described in this paper to be unequivocally established. Two other diamines, starting from (S)-proline and resolved 2-piperidine ethanol, were prepared using standard methods. These diamines lacked the bispidine framework of (-)-sparteine and were found to impart vastly inferior enantioselectivity. It was concluded that, for the asymmetric lithiation-substitution of N-Boc pyrrolidine, a rigid bispidine framework and only three of the four rings of (-)-sparteine are needed for high enantioselectivity. Furthermore, it is shown that diamine (1R,2S,9S)-11-methyl-7,11-diazatricyclo [7.3.1.02,7]tridecane is the first successful (+)-sparteine surrogate.

5-HT1F agonists

The present invention relates to a compound of formula (I): or a pharmaceutical acid addition salt thereof; which is useful for activating 5-HT1freceptors and inhibiting protein extravasation in a mammal.

4-[(4'-Methylphenyl)sulfonyl]-1-(trophenylphosphoranylidene)-2-butanone as a New Four-Carbon Synthon for Substituted Divinyl Ketones

The title compound and the corresponding anion have been conveniently used as precursors of substituted divinylketones in both carbo- and heterocyclization reactions in one-pot, three-step sequences leading to a wide variety of substituted carbo- and heterocyclic ring systems, as well as to multifunctionalized linear carbon frameworks. The compounds generated through the use of this multi-coupling reagent represent useful synthons for the construction of natural compounds including (+/-)-epibatidine, (-)-anabasine and (+/-)-pyrenophorin.

The hypoglycemic effect of (7R*,9aS*)-7-phenyl-octahydroquinolizin-2-one in mice

(-)-Multiflorine (1), which was isolated from leguminous plants, produced a hypoglycemic effect when administered to mice with streptozotocin-induced diabetes. (-)-Multiflorine has an enaminone type conjugation on the A-ring, which is unusual in lupine al

Indazole derivatives as 5-HT1F agonists

The present invention relates to a compound of formula or a pharmaceutical acid addition salt thereof; which are useful for activating 5-HT1F receptors and inhibiting neuronal protein extravasation in a mammal.

SUBSTITUTED HETEROAROMATIC 5-HT1F AGONISTS

This invention provides novel 5-HT 1F agonists of the Formula STR1 in which X, Y, E, R, A, B, and n are as defined in the specification, which are useful for the treatment of migraine and associated disorders.

Substituted heteroaromatic 5-HT 1F agonists

This invention provides novel 5-HT1Fagonists of the Formula in which X, Y, E, R, A, B, and n are as defined in the specification, which are useful for the treatment of migraine and associated disorders.