Cyclopentanone → Methyl 3-(cyclopentylamino)propanoate

Participants

Reaction Steps

Methyl 3-aminopropanoate (9.37 g, 0.09 mol) was solubilised in DCM (200 ml) and cyclopentanone (6.43 ml, 0.07 mol), sodium acetate (5.96 g, 0.07 mol) and sodium triacetoxyborohydride (22 g, 0.10 mol) were added. The reaction was stirred at rt for 16 h. 20% sodium bicarbonate (100 ml) and 2M sodium hydroxide (50 ml) were then added and the product extracted using DCM/H2O. The organic extracts were combined, washed with sat NaCl, dried using MgSO4, filtered and the filtrate evaporated under reduced pressure and further dried in vacuo to give the product as a pale yellow oil (8.90 g, 55%); MS+ve: 172.4.

Provenance & Evidence