Sodium Carbonate → tert-Butyl 4-[2-(trifluoromethyl)phenyl]-1,2,5,6-tetrahydropyridinecarboxylate

HRID 489668Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 489668
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1B(O)O.FC(F)(F)S(O[C:20]1[CH2:25][CH2:24][NH:23][CH:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:21]=1)(=O)=O.C(OC(N1CCC(=O)CC1)=O)(C)(C)C.[Li+].CC([N-]C(C)C)C.C1C=CC(N(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O)=CC=1.C([O-])([O-])=O.[Na+].[Na+]>O.COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:20]1[CH2:25][CH2:24][NH:23][CH:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:21]=1

Komponenten

10

Edukt 6

HCID 10340Sodium CarbonateHCID 142176Phenyl triflimideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 2724682Lithium diisopropylamideHCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 22266210Tert-butyl 4-[(trifluoromethyl)sulfonyloxy]-1,2,5,6-tetrahydropyridinecarboxylate

Produkt 1

HCID 22266248tert-Butyl 4-[2-(trifluoromethyl)phenyl]-1,2,5,6-tetrahydropyridinecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

The title compound was prepared according to the procedure described in Preparation A using 2-(trifluoromethyl)phenylboronic acid (Aldrich) (1.89 g, 10 mmol), tert-butyl 4-[(trifluoromethyl)sulfonyloxy]-1,2,5,6-tetrahydropyridinecarboxylate [prepared by the method of Wustrow, D. J. and Wise, L. D., Synthesis, 1991, 993-995, from tert-butyl-4-oxopiperidine-1-carboxylate (Aldrich), LDA (Aldrich) and N-phenyltrifluoromethanesulfonimide (Aldrich)] (3.64 g, 11 mmol), tetrakis(triphenylphosphine)palladium (0) (Strem Chemicals) (0.578 g, 0.5 mmol), LiCi (Aldrich) (1.27g, 30 mmol), and Na2CO3 (Aldrich) (2.46 g, 30 mmol) in water (15 mL) and DME (20 mL). Purification by silica gel chromatography (5:1 hexane:EtOAc) provided the title compound as a white foam (2.01 g). MS (ESI, pos. ion) m/z: 328 (M+1); MS (ESI, neg. ion) m/z: 326 (M−1). Calc'd for C17H20F3NO2: 327.34.

Aufarbeitung

  1. customThe title compound was prepared
  2. customprepared by the method of Wustrow, D
  3. custom, Synthesis, 1991, 993-995
  4. customPurification by silica gel chromatography (5:1 hexane:EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-62611c2b2fca4456a21b3f65b831c302
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06977264B2

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