Dexanabinone, Dexanabinol, PRS-211007, HU-211

1,1-二甲基庚基-11-羟基四氢大麻酚Chemical Name: (+)-7-Hydroxy-DELTA6-tetrahydrocannabinol dimethylheptyl homolog; (+)-(S,S)-6,6-Dimethyl-(1,1-dimethylheptyl)-1-hydroxy-9-(hydroxymethyl)-6a,7,10,10a-tetrahydro-6H-dibenzo[b,d]pyran
CAS No. 112924-45-5
项目整合开发状态: Phase III
项目研究机构: Pharmos (Orphan Drug), Pharmos (Originator)
合成路线:The Grignard reaction of ethyl heptanoate (I) with deuterated methylmagnesium iodide (II) in ether gives deuterated 2-methyl-2-octanol (III),which is treated with deuterium oxide to yield heptadeuterated 2-methyl-2-octanol (IV).The condensation of (IV) with monodeuterated 2,6-dimethoxyphenol (V) (obtained by treatment of 2,6-dimethoxyphenol (VI) with deuterium oxide) by means of deuterated trifluoromethylsulfonic acid affords the alkylated phenol (VII),which is phosphorylated with diethyl phosphite and triethylamine giving the phosphate (VIII).The reduction of (VIII) with Li/NH3 yields the deuterated dimethoxybenzene (IX),which is demethylated with boron tribromide in dichloromethane to afford the deuterated resorcinol (X).The condensation of (X) with alpha-pinene-3,10-diol 10-O-pivalic ester (XI) by means of boron trifluoride etherate in methylene chloride gives the deuterated target compound as its monopivalic ester (XII),which is finally treated with LiAlH4 in THF to eliminate the ester group.