1-Piperidinecarboxylic acid, 4-[(2-methoxyethyl)amino]-, phenylmethyl ester synthesis
- Product Name:1-Piperidinecarboxylic acid, 4-[(2-methoxyethyl)amino]-, phenylmethyl ester
- CAS Number:1067914-64-0
- Molecular formula:C16H24N2O3
- Molecular Weight:292.37
Yield:1067914-64-0 89%
Reaction Conditions:
Stage #1: benzyl 4-oxo-1-piperidinecarboxylate;2-methoxyethylamine in tetrahydrofuran;methanol at 20; for 1.5 h;
Stage #2: with methanol;sodium tetrahydroborate in tetrahydrofuran at 20; for 48 h;
Steps:
35.A
A solution of 2-methoxyethanamine (0.241 g, 3.22 mmol) and benzyl A- oxopiperidine-1-carboxylate (0.500 g, 2.14 mmol) in l0 ml of a l :l MeOH/THF mixture was stirred at ambient temperature under a nitrogen atmosphere for 1.5 hours. Sodium tetrahydroborate (243 mg, 6.42 mmol) was added, and the resulting mixture was stirred at ambient temperature for 48 hours. The reaction mixture was carefully diluted with saturated aqueous sodium carbonate solution (40 ml) and extracted thoroughly with DCM and EtOAc. The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated to afford an oil (0.56 g, 89 % yield) which was used directly in the next step.
References:
WO2008/121687,2008,A2 Location in patent:Page/Page column 51