Cyclopentylamine → Tert-butyl 2-(cyclopentylamino)acetate

Participants

Reaction Steps

To a solution containing 75 g (0.88 mol) of cyclopentylamine and 100 g (1.0 mol) of triethylamine in 500 ml of ether at 0° C. was slowly added 136 g (0.70 mol) of t-butyl bromoacetate in 200 ml of ether. After stirring at room temperature for 6 hours, the mixture was filtered, washed with water, and concentrated in vacuo. The residue was acidified with 5% aqueous HCl, washed with ether, rendered basic with 5% aqueous K2CO3, and extracted with ether. The ethereal solution was then washed with water, dried over MgSO4, and concentrated in vacuo to give 90 g (65%) of N-cyclopentylglycine, t-butyl ester as an oil which crystallized on standing.

Provenance & Evidence