Hydrochloric Acid → HCID 54274472, Verbindung

Reaktionsgleichung

[O:1]1[C:9]2[CH2:8][CH2:7][N:6]([S:10]([C:13]3[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=3)(=[O:12])=[O:11])[CH2:5][C:4]=2[CH:3]=[CH:2]1.B.Cl>O1CCCC1>[O:1]1[C:9]2[CH2:8][CH2:7][N:6]([S:10]([C:13]3[CH:21]=[CH:20][C:16]([CH2:17][OH:18])=[CH:15][CH:14]=3)(=[O:12])=[O:11])[CH2:5][C:4]=2[CH:3]=[CH:2]1

Komponenten

Versuchsvorschrift

To a suspension of 19.040 g (61.953 mmol) of 4-(6,7-dihydro-4H-furo[3,2-c]pyridin-5-ylsulfonyl)benzoic acid in 100 ml of tetrahydrofuran, 74.3 ml (74.3 mmol) of 1.0 M borane in tetrahydrofuran was added dropwise under ice-cooling, followed by overnight stirring at room temperature. Dilute hydrochloric acid was added, followed by stirring at room temperature for 0.5 hours and 3 extractions with ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The residue was dissolved in 50 ml of methanol; 15 ml of concentrated hydrochloric acid was added, followed by stirring at 70° C. for 1 hour. The reaction mixture was poured into water and extracted with ethyl acetate 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/1) to yield the desired product.