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Synthesis of 1-chloro-1-[15N]nitrosocyclohexane, an electrophilic aminating reagent

โœ Scribed by Siegfried N. Lodwig; Louis A. Silks III; Clifford J. Unkefer

Publisher
John Wiley and Sons
Year
1996
Tongue
French
Weight
331 KB
Volume
38
Category
Article
ISSN
0022-2135

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โœฆ Synopsis

We have prepared 1 -chloro-l-[15N]nitrosocyclohexane, an electrophillic aminating reagent useful for the stereoselective synthesis of a-[lsN]arnino acids. Treatment of potassium [15N]nitrate with PbO gave potassium [IsNInitrite, which was converted into the intermediate hydroxylamine disulfonate by treatment with sodium bisulfite and sulfur dioxide. Addition of an excess of cylohexanone followed by heating gave a mixture of the cyclohexanone [lsN]oxime and unreacted cyclohexanone which was removed in vacua The resulting [IsNIoxime was then converted to 1 -chloro-1 -[~~N]nitrosocyclohexane in essentially quantitative yield by treatment with chlorine gas .

๐Ÿ“œ SIMILAR VOLUMES

Stereoselective synthesis of stable isot
Stereoselective synthesis of stable isotope-labeled L-ฮฑ-amino acids: Electrophilic amination of Oppolzer's acyl sultams in the synthesis of L-[15N]alanine, L-[15N]valine, L-[15N]leucine, L-[15N]phenylalanine and L-[1-13C, 15N]valine
โœ Siegfried N. Lodwig; Clifford J. Unkefer ๐Ÿ“‚ Article ๐Ÿ“… 1996 ๐Ÿ› John Wiley and Sons ๐ŸŒ French โš– 475 KB ๐Ÿ‘ 1 views

Using 1 -chloro-l-[~~N]nitrosocyclohexane, we have prepared five L-[a-'SN]arnino acids. The stereoselective electophillic hydroxyamination of (S)-acylbornane-l0,2-suftams, followed by ZnO/H+ reduction, and alkaline cleavage of the chiral auxiliary, gave the amino acids in 97.2-99.5 % e.e. By starti