HMR-1556

N-[(3R,4S)-3,4-二氢-3-羟基-2,2-二甲基-6-(4,4,4-三氟丁氧基)-2H-1-苯并吡喃-4-基]-N-甲基甲磺酰胺Chemical Name: (+)-N-[2,2-Dimethyl-3(R)-hydroxy-6-(4,4,4-trifluorobutoxy)-3,4-dihydro-2H-1-benzopyran-4(S)-yl]-N-methylmethanesulfonamide; (+)-N-[2,2-Dimethyl-3(R)-hydroxy-6-(4,4,4-trifluorobutoxy)chroman-4(S)-yl]-N-methylmethanesulfonamide
CAS No. 223749-46-0, 223749-47-1 (enantiomer)
项目整合开发状态: Preclinical
项目研究机构: Aventis Pharma (Originator)
合成路线:Chromanone (II) was prepared by reaction of 2',5'-dihydroxyacetophenone (I) with acetone and pyrrolidine.Alkylation of the hydroxyl group of (II) with 4,4,4-trifluorobutyl bromide in the presence of NaH provided ether (III).The keto group of (III) was then reduced to alcohol (IV),which was subsequently dehydrated to chomene (V) by means of p-toluenesulfonic acid in hot toluene.Asymmetric epoxidation of (V) with NaOCl employing the chiral auxiliary (R,R)-bis(3,5-di-tert-butylsalicylidene)-1,2-diaminocyclohexane manganese (III) chloride furnished epoxide (VI).Finally,epoxide opening by the sodium salt of N-methyl methanesulfonamide afforded the title compound.