Reaktionsgleichung
IC1C=CC([C@H]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C@H:11]3[CH2:18][CH2:19][CH2:20][N:10]3C2)=CC=1.[Br:21][C:22]1[CH:32]=[CH:31][C:25]([CH:26]([OH:30])[C:27]([OH:29])=[O:28])=[CH:24][CH:23]=1.C1(C2CCCN2)C=CC=CC=1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>>[Br:21][C:22]1[CH:23]=[CH:24][C:25]([CH:26]([OH:30])[C:27]([O:29][N:10]2[CH2:20][CH2:19][CH2:18][CH:11]2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:28])=[CH:31][CH:32]=1Komponenten
Versuchsvorschrift
Trans-1,2,3,5,6,10b-hexahydro-6-(4'-iodophenyl)pyrrolo[2,1-a]isoquinoline (trans-6), was synthesized by a four step reaction sequence outlined in FIG. 1A. 4-Bromomandelic acid (1) was coupled with 2-phenylpyrrolidine (2) in the presence of BOP reagent to yield 2-phenylpyrrolidino 4-bromophenyl-α-hydroxyacetate (3). Upon treatment with PPA, the amide 3 was cyclized to the lactam (4) which was reduced with aluminum hydride to provide a pair of diastereomers (5) with a trans-to-cis ratio of 2. The desired trans-6-(4'-bromophenol)-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]-isoquinoline (trans 5) was separated by flash chromatography. Trans-5 was treated with butyllithium followed by iodination to afford trans-1,2,3,5,6,10b-hexahydro-6-(4'-iodophenyl) pyrrolo [2,1-a]isoquinoline (trans-6). Enantiomeric enriched (+)-(6S, 10bR)-1,2,3,5,6,10b-hexahydro-6-(4'-iodophenyl)pyrrolo[2,1-a]isoquinoline was obtained by the same reaction sequence starting with (+)-2(R)-phenylpyrrolidine.
Quellen und Nachweise
- ORD-Eintrag
- ord-c2690581f2f443af979d77579e3a153c
- Quelldatensatz
- uspto-grants-2000_12
- Patentnummer
- US06162417
Verknüpfte Notizen
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