Acrivastine → HCID 10360541, Verbindung

HRID 542502

Reaktionsgleichung

Reaktionsgleichung von HRID 542502
[N:1]1([CH2:6]/[CH:7]=[C:8](/[C:16]2[N:21]=[C:20](/[CH:22]=[CH:23]/[C:24]([OH:26])=[O:25])[CH:19]=[CH:18][CH:17]=2)\[C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>[Ni]>[N:1]1([CH2:6]/[CH:7]=[C:8](/[C:16]2[N:21]=[C:20]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])[CH:19]=[CH:18][CH:17]=2)\[C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

3

Edukt 1

HCID 5284514Acrivastine

Produkt 1

HCID 10360541HCID 10360541, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 935NickelKatalysator

Versuchsvorschrift

A solution of compound 2, vide supra, (3 g) in alcohol (100 mL) containing Raney nickel (1 g) was stirred under hydrogen at room temperature and pressure until the calculated quantity of hydrogen had been absorbed (ca. 45 minutes). The reduced ester was recovered by filtration and evaporation and purified by column chromatography on silica gel using petroleum ether as eluent. Butyllithium (10 mL, 1.64M in hexane) was added under nitrogen to a stirred suspension of triphenyl-2-pyrrolidinoethylphosphonium bromide (7.2 g) in dry toluene (75 mL) to prepare a Wittig reagent. Treatment of this ester with Wittig reagent by the method of Example 1 followed by saponification gave a mixture of two isomeric acids which were separated by fractional crystallization from ethyl acetate/petroleum ether mixtures. The less soluble E isomer, 3-{6-[3-Pyrrolidino-1-(4-tolyl)prop-1E-enyl]-2-pyridyl]-propionic acid (Compound B), melted at 156°-157°.

Aufarbeitung

  1. custompressure until the calculated quantity of hydrogen had been absorbed (ca. 45 minutes)
  2. filtrationThe reduced ester was recovered by filtration and evaporation
  3. custompurified by column chromatography on silica gel
  4. additionButyllithium (10 mL, 1.64M in hexane) was added under nitrogen to a stirred suspension of triphenyl-2-pyrrolidinoethylphosphonium bromide (7.2 g) in dry toluene (75 mL)
  5. customto prepare a Wittig reagent
  6. customgave
  7. additiona mixture of two isomeric acids which
  8. customwere separated by fractional crystallization from ethyl acetate/petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-8ce2272845cd4c67afe1d10432f4ba1b
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04657918

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