Ethanolamine → benzyl N-(2-hydroxyethyl)carbamate
Reaction equation
[NH2:1][CH2:2][CH2:3][OH:4].Cl[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[OH-].[Na+]>>[OH:4][CH2:3][CH2:2][NH:1][C:6](=[O:7])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1Participants
Procedure
It has already been disclosed that alkyl N-(hydroxy-alkyl)-carbamates can be obtained by reacting amino alcohols with chloroformates. This reaction is customarily carried out in an inert organic solvent in the presence of an acid acceptor at temperatures from -20° C. to +20° C. Examples which may be mentioned are the reaction of 2-methylamino-ethanol with benzyl chloroformate and triethylamine in chloroform at 20° C. (DE-A 3,239,390), of 2-(2-hydroxyethyl)-piperidine with butyl chloroformate and triethylamine in tetrahydrofuran at -20° C. (EP-A 289,842) and the reaction of 2,2-diethyl-3-hydroxypropylamine with ethyl chloroformate and triethylamine in benzene, with cooling, followed by refluxing for 2.5 hours (German Patent Specification 1,150,973). It is also known that 2-(2-hydroxyethyl)-piperidine can be reacted with methyl chloroformate at 0° to 20° C. in the presence of an aqueous sodium hydrogen carbonate solution to give methyl 2-(2-hydroxyethyl)-piperidinyl-carbamate (J. Chem. Soc. Perkin Trans. I 1988, 2251 to 2253). It is furthermore known that 2-aminoethanol can be reacted with benzyl chloroformate at 0° C. using 4N sodium hydroxide solution as acid acceptor to give benzyl N-(2-hydroxy-ethyl)-carbamate [J. Am. Chem. Soc. 69, 1384 (1947)].
Sources & evidence
- ORD record
- ord-50df9b5d942f40b8a607f382a7a51eaa
- Source dataset
- uspto-grants-1994_04
- Patent number
- US05304650
Reaction notes
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