ETHYL 1-CBZ-PIPERIDINE-2-CARBOXYLATE

1-Benzyl 2-ethyl piperidine-1, 2-dicarboxylate; To a stirred solution of ethyl piperidine-2-carboxylate (15 g, 95 mmol), triethylamine (27 ml, 191 mmol) and 4-dimethylaminopyridine (0.58 g, 4.8 mmol) in dichloromethane (100 ml) at 0°C is added a solution of benzyl chloridocarbonate (17 g, 100 mmol) dropwise. The reaction is allowed to warm slowly to room temperature. It is stirred at room temperature overnight (16 h), then allowed to stand for 2 days. The crude product is extracted with dichloromethane, washed with 1 N hydrochloric acid, saturated aqueous sodium bicarbonate solution and brine. The organic phase is dried with anhydrous magnesium sulfate, filtered and concentrated ira vacuo. The residue is purified by flash chromatography over silica gel 60 (300 g) with cyclohexane/ethyl acetate as eluent to afford a pale yellow oil. Yield: 17. 9 g (62percent of th.) HPLC (method 6): Rt = 4.91 min, A. max = 202 nm MS (ESIpos): m/z= 309 (M+NH4) +Example 9A; 1-Benzyl 2-ethyl piperidine-1, 2-dicarboxylate; To a stirred solution of ethyl piperidine-2-carboxylate (15 g, 95 mmol), triethylamine (27 ml, 191 mmol) and 4-dimethylaminopyridine (0.58 g, 4.8 mmol) in dichloromethane (100 ml) at 0C is added a solution of benzyl chloridocarbonate (17 g, 100 mmol) dropwise. The reaction is allowed to warm slowly to room temperature. It is stirred at room temperature overnight (16 h), then allowed to stand for 2 days. The crude product is extracted with dichloromethane, washed with 1 N hydrochloric acid, saturated aqueous sodium bicarbonate solution and brine. The organic phase is dried with anhydrous magnesium sulfate, filtered and concentrated ira vacuo. The residue is purified by flash chromatography over silica gel 60 (300 g) with cyclohexane/ethyl acetate as eluent to afford a pale yellow oil. Yield: 17. 9 g (62% of th.) HPLC (method 6): Rt = 4.91 min, A. max = 202 nm MS (ESIpos): m/z= 309 (M+NH4) +

Molecular Weight:291.34
XLogP3:2.8
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:291.14705815
Monoisotopic Mass:291.14705815
Topological Polar Surface Area:55.8
Heavy Atom Count:21
Complexity:352
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes