1952
DOI: 10.1021/ja01135a034
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2-, 3- and 4-(1-Methylpiperidyl)-carbinols and Derivatives

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Cited by 20 publications
(2 citation statements)
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“…The following starting compounds were prepared according to the previously described methods: sodium 6-chloropyridin-2-ylthiolate [1] , 2-chloromethyl-1-methylpiperidine [15] , 3-chloromethyl-1-methylpiperidine [16] , 3-chloromethyl-1-methylpyrrolidine [17] , tosylate of 3α-mesyloxy-8-methyl-8-azabicyclo[3.2.1]octane (tosylate of 3α-tropinemethanesulfonate) [18] , 2bromo-6-chloropyridine [19] .…”
Section: General Methodsmentioning
confidence: 99%
“…The following starting compounds were prepared according to the previously described methods: sodium 6-chloropyridin-2-ylthiolate [1] , 2-chloromethyl-1-methylpiperidine [15] , 3-chloromethyl-1-methylpiperidine [16] , 3-chloromethyl-1-methylpyrrolidine [17] , tosylate of 3α-mesyloxy-8-methyl-8-azabicyclo[3.2.1]octane (tosylate of 3α-tropinemethanesulfonate) [18] , 2bromo-6-chloropyridine [19] .…”
Section: General Methodsmentioning
confidence: 99%
“…Subsequent reduction of 15 with LiAlH 4 provided alcohol 16 in 84 % yield. This compound is an important building block in the preparation of pharmaceuticals in order to improve water solubility; this newly developed synthesis is superior to known procedures [30][31][32][33] and allows the synthesis of this compound from commercially available ethyl isonipecotate (14) in two steps with 84 % overall yield. For the synthesis of 21, alcohol 16 was treated with 1-chloro-4-nitrobenzene (17) in a nucleophilic aromatic substitution to give 18 in 83 % yield.…”
Section: Introductionmentioning
confidence: 99%