Chemical Properties
White powder
Uses
1-Boc-D-nipecotic acid is used as an organic chemical synthesis intermediate.
reaction suitability
reaction type: Boc solid-phase peptide synthesis
Synthesis
Step 1: 3-Piperidinecarboxylic acid (1.05 g, 8.1 mmol) was dissolved in a solvent mixture of tetrahydrofuran (20 mL) and water (20 mL). Di-tert-butyl dicarbonate (2.48 g, 11.4 mmol) and sodium bicarbonate (0.96 g, 11.4 mmol) were added. The reaction mixture was stirred at room temperature overnight. After the reaction was completed, the mixture was diluted with water and ether. The aqueous layer was adjusted to pH=2 with concentrated hydrochloric acid and then extracted with dichloromethane. The organic layers were combined, dried over sodium sulfate, and concentrated to give (R)-1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid (1.8 g, 97% yield). retention time by LCMS (Condition A) = 3.26 min, and m/z = 230 ([M+H]+) was observed by mass spectrum.
References
[1] Patent: WO2005/14540, 2005, A1. Location in patent: Page/Page column 39
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 19, p. 6456 - 6468
[3] Patent: WO2010/120889, 2010, A1. Location in patent: Page/Page column 55; 60
