(R)-1-Boc-3-Aminopiperidine

Chemical Properties

Yellow liquid

Uses

(R)-3-Amino-1-Boc-piperidine can be used to prepare a benzoxazepine derivative named (R)-7-(3,5-dimethoxyphenyl)-N-(piperidin-3-yl)-4-propionyl-2,3,4,5-tetrahydro-1,4-benzoxazepine-9-carboxamide, a potent CBP/P300 bromodomain inhibitor.

Uses

(R)-(-)-3-Amino-1-Boc-piperidine(tert-Butyl (R)-3-Aminopiperidine-1-carboxylate), is an heterocyclic building block used for the synthesis of more complex pharmaceutical compounds. It is also found to act as a γ-secretase modulators, and a potent structure for lowering Ab42 production in both in vitro and in vivo.

General Description

(R)-3-Amino-1-Boc-piperidine can be used as a precursor for the preparation of dipeptidyl peptidase IV inhibitors like linagliptin, alogliptin, and other antidiabetic agents.

Synthesis

The general procedure for the synthesis of (R)-1- tert-butyl tert-butyloxycarbonyl-3-aminopiperidine from (R)-3-carbamoylpiperidine-1-carboxylic acid is as follows: in Example 28, (R)-1-(tert-butoxycarbonyl)-3-aminopiperidine was prepared as follows: firstly, (R)-1-(tert-butoxycarbonyl)piperidine amide (9 g of a solution, wherein the net weight of (R)-1 -(tert-butoxycarbonyl)piperidine amide is 0.7 g), sodium hydroxide (1.3 g, 10 equiv) and sodium hypochlorite aqueous solution (2.2 g, 10 equiv) are combined. Oxycarbonyl)piperidinamide has a net weight of 0.7 g), sodium hydroxide (1.3 g, 10 eq.) and aqueous sodium hypochlorite (2.2 g, 1.1 eq.) were mixed. The reaction mixture was stirred at 15 to 25°C for 16 hours. Upon completion of the reaction, the aqueous layer was separated and removed, followed by evaporation of the solvent under reduced pressure. Toluene (10 mL) and saturated brine (5 mL) were added to the residue and the aqueous layer was again separated and removed. Finally, the solvent was evaporated under reduced pressure to afford (R)-1-tert-butoxycarbonyl-3-aminopiperidine, the product was a yellow oil (0.7 g, net weight: 0.5 g, yield: 80%).

References

[1] Patent: US2010/105917, 2010, A1. Location in patent: Page/Page column 21