Hydrochloric Acid → 6-[3-Adamantan-1-yl-4-(tert-butyl-dimethyl-silanyloxy)-benzoyloxy]-nicotinic acid

HRID 1643

Reaktionsgleichung

Reaktionsgleichung von HRID 1643
[C:1]12([C:11]3[CH:12]=[C:13]([CH:29]=[CH:30][C:31]=3[O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[C:14]([O:16][C:17]3[CH:28]=[CH:27][C:20]([C:21]([O:23]CC=C)=[O:22])=[CH:19][N:18]=3)=[O:15])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C([SnH](CCCC)CCCC)CCC.Cl>O1CCCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]12([C:11]3[CH:12]=[C:13]([CH:29]=[CH:30][C:31]=3[O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:34])[CH3:35])[C:14]([O:16][C:17]3[CH:28]=[CH:27][C:20]([C:21]([OH:23])=[O:22])=[CH:19][N:18]=3)=[O:15])[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 5948TributylstannaneHCID 21846704Allyl 6-[3-adamantan-1-yl-4-(tert-butyl-dimethyl-silanyloxy)-benzoyl-oxy]-nicotinate

Produkt 1

HCID 218467136-[3-Adamantan-1-yl-4-(tert-butyl-dimethyl-silanyloxy)-benzoyloxy]-nicotinic acidAusbeute 22,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

100 mg of this ester were dissolved in 5 ml of absolute tetrahydrofuran and treated under argon with 104 mg of tetrakis-(triphenylphosphine)-palladium and 61 mg of tributyltin hydride. After stirring at room temperature for 30 min., the reaction mixture was poured on to ice/saturated ammonium chloride solution, acidified with 1N hydrochloric acid and extracted with ethyl acetate. The dark oil obtained after drying and evaporation was purified by chromatography (RP18-LiChroprep, acetonitrile) and recrystallization from ethyl acetate. There were obtained 21 mg of 6-[3-adamantan-1-yl-4-(tert-butyl-dimethyl-silanyloxy)-benzoyloxy]-nicotinic acid in colorless crystals, m.p. 188°-190° C.

Aufarbeitung

  1. additionthe reaction mixture was poured on to ice/saturated ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. customThe dark oil obtained
  4. customafter drying
  5. customevaporation
  6. customwas purified by chromatography (RP18-LiChroprep, acetonitrile) and recrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-429d4cda5f5a43799ceb5fbb3c399100
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726191

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