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TERT-BUTYL 4-[(2Z)-2-AMINO-2-(HYDROXYIMINO)ETHYL]PIPERIDINE-1-CARBOXYLATE synthesis

4synthesis methods
256411-39-9 Synthesis
(1-BOC-piperidin-4-yl)acetonitrile

256411-39-9
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TERT-BUTYL 4-[(2Z)-2-AMINO-2-(HYDROXYIMINO)ETHYL]PIPERIDINE-1-CARBOXYLATE

713147-49-0
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Yield:713147-49-0 81.36%

Reaction Conditions:

with hydroxylamine hydrochloride;potassium carbonate in ethanol;water at 20; for 48 h;

Steps:

16

4-Cyanomethyl-piperidine-1 -carboxylic acid ferf-butyl ester (compound of Example 15; 2.3 g, 10.2 mmol), anhydrous potassium carbonate (2.27 g, 16.4 mmol) and hydroxylamine hydrochloride (2.14 g, 30.8 mmol) in ethanol: water (25 : 4 ml.) was stirred at room temperature for 48 h. The reaction mixture was filtered, solvent evaporated and the residue obtained was purified by column chromatography (silica gel, 8 % ethyl acetate in petroleum ether) to afford the title compound.Yield: 2.14 g (81 .36 %); 1 H NMR (MeOD, 300 MHz): δ 4.04 (m, 2H), 2.73 (m, 2H), 1 .99 (d, 2H), 1 .77 (m, 1 H), 1 .67 (m, 2H), 1 .44 (s, 9H), 1 .10 (m, 2H); MS (ES+): 258 (M+1 ).

References:

WO2011/104680,2011,A1 Location in patent:Page/Page column 74