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250372-00-0

tert-Butyl 4-(4-amino-2-fluorophenoxy)piperidine-1-carboxylate synthesis

5synthesis methods
-

Yield:250372-00-0 97%

Reaction Conditions:

palladium in methanol;hexane;

Steps:

R.23 4-(1-t-Butoxycarbonylpiperidin-4-yloxy)-3-fluoroaniline

Reference Example 23 4-(1-t-Butoxycarbonylpiperidin-4-yloxy)-3-fluoroaniline To a solution of 4-(1-t-butoxycarbonylpiperidin-4-yloxy)-3-fluoronitrobenzene (3.71 g) in methanol (50 ml) was added palladium on carbon (0.30 g) and the mixture was stirred under a hydrogen atmosphere at room temperature for 4 hours. The reaction mixture was filtered and the filtrate concentrated in vacuo. The residue was purified by chromatography on a silica gel column using hexane/ethyl acetate=1/1 as an eluant to give the desired compound (3.27 g, yield 97%) as a pale red solid. 1H NMR (500 MHz, CDCl3) δ ppm: 1.46 (9H, s), 1.72 (2H, m), 1.86 (2H, m), 3.23 (2H, m), 3.75 (2H, m), 4.17 (1H, m), 6.35 (1H, dd, J=8.5, 3.0), 6.44 (1H, dd, J=12.5, 3.0), 6.82 (1H, dd, J=9.0, 8.5).

References:

US6555556,2003,B1