4-AMINO-PIPERIDINE-1-CARBOXYLIC ACID BENZYL ESTER

4_(N-BOC amino)-CBz piperidine (24.4 kg 73.42 mol), THF (65 kg) and 5 M HCl (23.0 kg, 110.13 mol) were combined and heated to 30 -35 A mixture of phenylmethyl 4-(l, 3-dioxo- l, 3-dihydro-2H-isoindol-2-yl)-l -piperidinecarboxylate (1.5 g, 4.11 mmoles) and 25percent hydrazine hydrate (10.0 mL) in ethanol (20 mL) was heated under reflux for 30 minutes. The mixture was evaporated, re-diluted with ethanol and re-evaporated to a solid. The solid was slurried in diethyl ether, collected, washed with diethyl ether and the filtrate evaporated to give the title compound as an oil (quant.) 1η NMR (400 MHz, CHLOROFORM-, /) δ ppm 7.25 - 7.45 (m, 5 H), 5.14 (s, 2 H), 4.89 - 5.07 (m, 1 H), 3.18 - 3.42 (m, 2 H), 2.76 - 2.95 (m, 2 H), 1.74 - 1.94 (m, 2 H), 1.51 - 1.68 (m, 2 H), 1.28 (d, J=6.06 Hz, 2 H).To a solution of 4-methyl-2-methylsulfanyl-pyrimidine-5-carboxylic acid (3.0 g, 16 mmol) in DMF (5 mL) was added HATU ((dimethylamino)-N, N-dimethyl(3H-[l, 2, 3]tri- azolo[4, 5-b]yridine-3-yloxy)methaniminium hexafluorophosphate; 7.4 g, 20 mmol). The mixture was stirred at RT for 3 hours. Benzyl 4-aminopiperidine-l-carboxylate (4.2 g, 18 mmol) and DIPEA (8.4 g, 65 mmol, 11.4 mL) were then added in the mixture before stirring at RT for 3 hours. Upon completion, the reaction mixture was quenched with water (50 mL), diluted with EtOAc (30 mL) and extracted with EtOAc (30 mL x 3). The organic layers were combined, washed with brine (10 mL x 3), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography to give the tittle compound (6.0 g, 92% yield).

Molecular Weight:234.29
XLogP3:1.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:234.136827821
Monoisotopic Mass:234.136827821
Topological Polar Surface Area:55.6
Heavy Atom Count:17
Complexity:244
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes