R-137696

Chemical Name: (-)-1-[3-[3,4-Dihydro-2H-1-benzopyran-2(R)-ylmethylamino]propyl]perhydropyrimidin-2-one
CAS No. 227296-56-2, 227296-61-9 ((S)-isomer), 227296-62-0 ((S)-isomer, oxalate (1:1)), 227296-58-4 (L-tartrate), 227296-57-3 (oxalate), 227296-54-0 (racemate)
项目整合开发状态: Clinical
项目研究机构: Janssen (Originator)
合成路线:Racemic 3,4-dihydro-2H-1-benzopyran-2-carboxylic acid (I) is resolved into the corresponding enantiomers by recrystallization of the diastereomeric salts with (+)-(R)-alpha-methylbenzylamine,and the desired (R)-carboxylic acid is further esterified with H2SO4/EtOH to furnish the ethyl ester (II).Subsequent reduction of ester (II) with NaBH4 in toluene/EtOH leads to alcohol (III),which is converted into mesylate (IV) employing methanesulfonyl chloride and triethylamine.Mesylate (IV) is finally condensed with 1-(3-aminopropyl)-hexahydro-2-pyrimidinone (V) by heating with CaO at 100 C in THF in an autoclave to provide the title compound