Reaktion #716535

Reaktionsgleichung

methyl 5-(4-(1H-pyrazol-1-yl)benzyl)-4-cyclopropyl-2-formylbenzoate

trans-2-aminocyclopentanol hydrochloride

triethylamine

magnesium sulfate

→

title compound

Ausbeute 49.9%

rac-5-cyclopropyl-2-(trans-2-hydroxycyclopentyl)-6-(4-(1H-pyrazol-1-yl)benzyl)isoindolin-1-one

Ausbeute 49.9%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe insoluble substance was removed by filtration
2. 2
   Einengenthe filtrate was concentrated under reduced pressure
3. 3
   workup.ADDITIONThe residue was diluted with methanol (2.20 mL) and THF (2.20 mL), sodium triacetoxyborohydride (0.13 g)
4. 4
   workup.ADDITIONwas added
5. 5
   workup.ADDITIONThe reaction mixture was diluted with ethyl acetate
6. 6
   Waschenthe mixture was washed with water and saturated brine
7. 7
   TrocknenThe organic layer was dried over anhydrous magnesium sulfate
8. 8
   Sonstigethe solvent was evaporated under reduced pressure
9. 9
   SonstigeThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Vorschrift

A solution of methyl 5-(4-(1H-pyrazol-1-yl)benzyl)-4-cyclopropyl-2-formylbenzoate (0.11 g), trans-2-aminocyclopentanol hydrochloride (0.04 g), triethylamine (0.04 mL) and anhydrous magnesium sulfate (0.07 g) in THF (2.20 mL) was stirred at room temperature for 5 hr. The insoluble substance was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was diluted with methanol (2.20 mL) and THF (2.20 mL), sodium triacetoxyborohydride (0.13 g) was added thereto, and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, and the mixture was washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.06 g).

Quelle