ChemicalBook CAS DataBase List N-BOC-piperidine-4-carboxylic acid

N-BOC-piperidine-4-carboxylic acid synthesis

14synthesis methods

Product Name:N-BOC-piperidine-4-carboxylic acid
CAS Number:84358-13-4
Molecular formula:C11H19NO4
Molecular Weight:229.27

498-94-2 Synthesis

498-94-2
0 suppliers
$5.00/10g

24424-99-5 Synthesis

24424-99-5
850 suppliers
$13.50/25G

84358-13-4
391 suppliers
$5.00/5g

Yield:84358-13-4 100%

Reaction Conditions:

in sodium hydroxide;tert-butyl alcohol

Steps:

60 Scheme G, step a: 1,4-Piperidinedicarboxylic acid, 1-(11-dimethylethyl)ester (14)
EXAMPLE 60 Scheme G, step a: 1,4-Piperidinedicarboxylic acid, 1-(11-dimethylethyl)ester (14) To a solution of 4-piperidinecarboxylic acid (13) (700 g, 5.42 mol) in aqueous NaOH (1N, 6.5 L) and t-butanol (6.5 L) at 0° C. was added di-t-butyldicarbonate (1295.8 g, 5.94 mol) slowly over 30 minutes. The reaction mixture was stirred overnight at ambient temperature. The resulting solution was concentrated (48° C./20 torr) to half of its volume and quenched by the addition of HCl (10%, 2.6 L). The white solid which precipitated was filtered off, washed with water (1L) and air-dried to give the title compound (14) (1178 g, 100% yield); m.p. 144-146° C. ¹H NMR (CDCl₃) δ 4.1 (d, 2H, J=12.0 Hz), 2.91 (t, 2H, J=12.0 Hz), 2.5 (m, 1H), 2.0 (m, 2H), 1.7 (m, 2H), 1.52 (s, 9H).

References:

Daugs, Edward D.;Evans, Jonathan C.;Flemming, Hans-Wolfram;Hilpert, Thomas Heinz Eduard;Koek, Johannes Nicolaas;Laskovics, Frederick M.;Stolz-Dunn, Sandra K.;Tomlinson, Ian A. US2002/151717, 2002, A1

FullText

124443-68-1 Synthesis