JNJ-17297709
Chemical Name: (2R*,3aR*,12bS*)-N,N-Dimethyl-N-(3,3a,8,12b-tetrahydro-2H-dibenzo[3,4:6,7]cyclohepta[1,2-b]furan-2-ylmethyl)amine
CAS No. 198644-59-6 (no stereoch. at 2), 198644-93-8 (undefined isomer)
项目整合开发状态: Preclinical
项目研究机构: Johnson & Johnson (Originator)
合成路线:Reduction of dibenzosuberenone (I) with in situ generated AlH3 affords dibenzocycloheptene (II).Subsequent epoxidation of (II) employing m-chloroperbenzoic acid gives the dibenzocycloheptaoxirane (III) (1).Epoxide ring opening in (III) with allylmagnesium bromide produces the trans alcohol (IV).Bromination of the double bond of (IV) with pyridinium tribromide leads to the trans-fused tetrahydrofuran derivative (V) as a mixture of 4 diastereoisomers.Then,substitution of the bromide ion of (V) with dimethylamine,followed by chromatographic separation of the isomers provides the target compound.
📌 参考资料/链接：
参考文献标题:Substd.tetracyclic tetrahydrofuran derivs.
文献作者:Gil-Lopetegui,P.; Fern醤dez-Gadea,F.J.; Meert,T.F.(Janssen Pharmaceutica NV)
参考来源:EP 0892793; JP 2000508327; WO 9738991
📄 详细内容
合成路线:Reduction of dibenzosuberenone (I) with in situ generated AlH3 affords dibenzocycloheptene (II).Subsequent epoxidation of (II) employing m-chloroperbenzoic acid gives the dibenzocycloheptaoxirane (III) (1).Epoxide ring opening in (III) with allylmagnesium bromide produces the trans alcohol (IV).Bromination of the double bond of (IV) with pyridinium tribromide leads to the trans-fused tetrahydrofuran derivative (V) as a mixture of 4 diastereoisomers.Then,substitution of the bromide ion of (V) with dimethylamine,followed by chromatographic separation of the isomers provides the target compound.
参考文献标题:Synthesis of 2-aminomethyl-3,3a,8,12b-tetrahydro-2H-dibenzocyclohepta[1,2-b]furan derivatives as potential anxiolytic agents
文献作者:Alonso,J.M.; Andr閟,J.I.; Cid,J.M.; et al.
参考来源:Drugs Fut 2002,27(Suppl.A),