Vildagliptin, LAF-237, NVP-LAF-237

维达列汀Chemical Name: 1-[2-(3-Hydroxyadamant-1-ylamino)acetyl]pyrrolidine-2(S)-carbonitrile
CAS No. 274901-16-5, 565453-38-5 (deleted CAS)
项目整合开发状态: Phase III
项目研究机构: Novartis (Originator)
合成路线:The reaction of adamantan-1-amine (I) with HNO3 and H2SO4 gives 3-nitroadamantan-1-amine (II),which is hydrolyzed with KOH in hot water to yield 3-hydroxyadamantan-1-amine (III).On the other hand,the reaction of chloroacetyl chloride (IV) with L-prolinamide (V) by means of K2CO3 in THF gives 1-(chloroacetyl)-L-prolinamide (VI),which is treated with trifluoroacetic anhydride in THF to yield the corresponding nitrile (VII).Finally 3-hydroxyadamantan-1-amine (III) is condensed with the 1-(chloroacetyl)-L-prolinenitrile (VII) by means of K2CO3 in dichloromethane to afford the target adamantane derivative.