3-Trifluoromethylcinnamic acid → 3-(3-Trifluoromethylphenyl)propanoic acid

HRID 476310

Reaktionsgleichung

Reaktionsgleichung von HRID 476310
C[C@@H](NCCCC1C=CC=C(C(F)(F)F)C=1)C1C=CC=C2C=CC=CC=12.Cl.[F:28][C:29]([F:42])([F:41])[C:30]1[CH:31]=[C:32]([CH:38]=[CH:39][CH:40]=1)[CH:33]=[CH:34][C:35]([OH:37])=[O:36]>[OH-].[Pd+2].[OH-]>[F:28][C:29]([F:41])([F:42])[C:30]1[CH:31]=[C:32]([CH2:33][CH2:34][C:35]([OH:37])=[O:36])[CH:38]=[CH:39][CH:40]=1

Komponenten

4

Edukt 2

HCID 855273-Trifluoromethylcinnamic acidHCID 156418Cinacalcet Hydrochloride

Produkt 1

HCID 27776833-(3-Trifluoromethylphenyl)propanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 9942167Palladium hydroxideKatalysator

Versuchsvorschrift

Tetrahedron letters, (49), 13-15, (2008), discloses a synthetic sequence to Cinacalcet hydrochloride comprising reduction of 3-(trifluoromethyl)cinnamic acid in the presence of palladium hydroxide to obtain 3-(3-trifluoromethylphenyl)-propanoic acid, which is coupled with (R)-1-(1-naphthyl)ethylamine to the corresponding amide. The amide is then reduced in the presence of boron trifluoride-THF and sodium borohydride as reducing agents. After complete conversion, the resulting amine-borane complex is hydrolyzed by the addition of water and the crude Cinacalcet extracted into toluene is reacted with hydrochloric acid to give Cinacalcet hydrochloride, according to the following Scheme 5:

Quellen und Nachweise

ORD-Eintrag
ord-c1e82025c42c46fe97994cddcaf2f627
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637708B2

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