1-methyl-1H-1,3-benzodiazole-2-carbaldehyde → 6-Cyclopentyl-6-[2-(3-fluoro-4-isopropoxy-phenyl)-ethyl]-4-hydroxy-3-(1-methyl-1H-benzoimidazol-2-ylmethyl)-5,6-dihydro-pyran-2-one

Reaktionsgleichung

[CH:1]1([C:6]2([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH:23]([CH3:25])[CH3:24])=[C:18]([F:26])[CH:17]=3)[O:11][C:10](=[O:12])[CH2:9][C:8](=[O:13])[CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:27][N:28]1[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[N:30]=[C:29]1[CH:37]=O.[Al+3].[Cl-].[Cl-].[Cl-]>>[CH:1]1([C:6]2([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH:23]([CH3:24])[CH3:25])=[C:18]([F:26])[CH:17]=3)[O:11][C:10](=[O:12])[C:9]([CH2:37][C:29]3[N:28]([CH3:27])[C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=4[N:30]=3)=[C:8]([OH:13])[CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

Edukt 3

HCID 7620841-methyl-1H-1,3-benzodiazole-2-carbaldehyde

HCID 6451240Aluminum(III) Chloride

HCID 160761116-(3-fluoro-4-isopropoxyphenethyl)-6-cyclopentyl-dihydro-3H-pyran-2,4-dione

Produkt 1

HCID 587624596-Cyclopentyl-6-[2-(3-fluoro-4-isopropoxy-phenyl)-ethyl]-4-hydroxy-3-(1-methyl-1H-benzoimidazol-2-ylmethyl)-5,6-dihydro-pyran-2-one

Versuchsvorschrift

The title compound was prepared by coupling 6-Cyclopentyl-6-[2-(3-fluoro-4-isopropoxy-phenyl)-ethyl]-dihydro-pyran-2,4-dione from Step 1 of Example B(14), to 1-Methyl-1H-benzoimidazole-2-carbaldehyde using the AlCl3/reduction procedure described for Example B(13). 1H NMR (CDCl3): δ 1.32 (d, J=6 Hz, 6H), 1.45-1.91 (brm, 8H), 2.05 (m, 2H), 2.44-2.88 (m, 8H), 2.91 (s, 3H), 4.48 (m, 1H), 6.75-6.92 (m, 3H) 7.22-7.45 (m, 3H) 7.66 (s, 1H). ESIMS (MH+): 507.2