tert-butyl N-[2-(4-hydroxypiperidin-4-yl)ethyl]carbamate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound (71 mg, 26%) was prepared as a yellow solid according to Example 1, except substituting the following three reagents: 1,1-dimethylethyl [2-(4-hydroxy-4-piperidinyl)ethyl]carbamate (1.5 g, 6.15 mmol) [prepared according to Example 20] for 1,1-dimethylethyl [2-(1-piperazinyl)ethyl]carbamate, 4-bromo-3-fluoro-6-(methyloxy)quinoline (1.57 g, 6.15 mmol) for 8-bromo-7-fluoro-2-(methyloxy)-1,5-naphthyridine and 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehyde (100 mg, 0.564 mmol) for 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carbaldehyde: LCMS (ES) m/e 482 (M+H)+; 1H NMR (400 MHz, CD3OD) δ 8.47 (d, J=4.6 Hz, 1H), 7.87 (d, J=9.1 Hz, 1H), 7.39 (d, J=2.7 Hz, 1H), 7.33 (dd, J=2.7, 6.3 Hz, 1H), 7.28 (d, J=8.0 Hz, 1H), 6.99 (d, J=8.0 Hz, 1H), 4.65 (s, 2H), 3.96 (s, 3H), 3.81 (s, 3H), 3.55-3.61 (m, 2H), 3.26-3.29 (m, 2H), 2.88-2.91 (m, 2H), 1.80-1.93 (m, 6H).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 1,1-dimethylethyl {2-[4-hydroxy-1-(phenylmethyl)-4-piperidinyl]ethyl}carbamate (3.2 g, 9.5 mmol) and Pd(OH)2 (1.92 g, 60 wt %) in EtOH (50 mL) was hydrogenated using a Parr Shaker under 50 psi. After 12 h, the solution was filtered through Celite® and concentrated yielding the title compound (2.33 g, quant.) as a yellow oil: LCMS (ES) m/e 245 (M+H)+. the solution was filtered through Celite® concentrated