N-Boc-2-piperidinecarboxylic acid

White crystalline powder

A solution of DL-pipecolinic acid (13 g, 100 mmol), potassium carbonate (55.2 g, 400 mmol), di-tert-butyl dicarbonate (28. 4 g, 130 mmol) in acetone (30 mL) and water (100 mL) was stirred at room temperature overnight. The reaction mixture was brought to [PH-] 3 using hydrochloric acid (1 N aqueous) and then extracted with ethyl acetate (350 mL). The organic phase was separated, sequentially washed with water (200 mL) and brine (200 mL), dried (sodium sulfate), filtered and concentrated in vacuo. The isolated solid was triturated with hexanes to yield 22.7 g (99percent) of the title compound as a white [SOLID. LH-] NMR [(CDC13), ] [8] [(PPM)] : 9.3 (bs, 1H), 4.84 (bd, 1H), 3.94 (m, 1H), 2.93 (m, 1H), 2.22 (m, 1H), 1.67 (m, 3H), 1.45 (m, [11H).]To a suspension of pipecolinic acid (1.0 mmol) in dioxane:water (4.5:1.5 mL) , Et3N (1.0 mmol) was added and the resulting mixture was stirred for 10 min. Then, a solution of (BOC)2O (1.10 mmol) in 1 mL of dioxane was added dropwise and the mixture was stirred at room temperature for 24 h. The solvent was evaporated under reduced pressure, and the residue was dissolved in EtOAc (30 mL). The solution was washed with 5percent HCl (15 mL), and brine (3 x 15 mL). After the last washing procedure the pH of the aqueous layer has to be >5. The organic phase was dried over MgSO4, filtered and concentrated in vacuum. The product, 1-(tert-butoxycarbonyl)piperidine-2-carboxylic acid (white solid, 70percent yield)2 was used to the next step without further purification.Piperidine-1, 2-dicarboxylic acid 1-tert-butyl ester (1). Piperidine-1, 2-dicarboxylic acid 1-tert-butyl ester (1).

Molecular Weight:229.27
XLogP3:1.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:229.13140809
Monoisotopic Mass:229.13140809
Topological Polar Surface Area:66.8
Heavy Atom Count:16
Complexity:282
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes