Triethylamine → HCID 178489256, Verbindung

To a mixture of 3-t-butyl-5-[4-(3-carboxy-5-isoxazolyl)phenyl]-4-(2-methoxyphenyl)-4,5-dihydro-1H-pyrrolo[3,4-c]pyrazol-6-one (0.080 g, 0.17 mmol), triethylamine (0.031 mL, 0.22 mmol) and THF (2 mL), ethyl chlorocarbonate (0.019 mL, 0.20 mmol) was added under ice-cooling conditions and the mixture stirred at r.t. for 2 hr. Sodium borohydride (0.026 g, 0.68 mmol), water (0.3 mL) and methanol (1 mL) were added to the mixture and the mixture was stirred at r.t. for 10 min. Water was added to the mixture, the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, saturated sodium bicarbonate and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was crystallized from dichloromethane, diethyl ether and ethyl acetate, and the precipitate was collected by filtration to give 3-t-butyl-5-[4-(3-hydroxymethyl-5-isoxazolyl)-phenyl]-4-(2-methoxyphenyl)-4,5-dihydro-1H-pyrrolo[3,4-c]pyrazol-6-one (0.068 g, 88%) as colorless crystals.

1. additionwas added under ice-
2. temperaturecooling conditions
3. stirringthe mixture was stirred at r.t. for 10 min
4. extractionthe mixture was extracted with ethyl acetate
5. washThe organic layer was washed with 1N hydrochloric acid, saturated sodium bicarbonate and brine
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was crystallized from dichloromethane, diethyl ether and ethyl acetate
9. filtrationthe precipitate was collected by filtration

ORD-Eintrag

ord-efa31dfca9b643b88a88a3ce21ae2c2d

Quelldatensatz

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08497263B2