Sodium Carbonate → tert-Butyl 4-(2-acetylphenyl)-1,2,5,6-tetrahydropyridinecarboxylate

HRID 489673Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 489673
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1B(O)O)(=[O:3])[CH3:2].FC(F)(F)S(O[C:19]1[CH2:24][CH2:23][NH:22][CH:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:20]=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.[Li+].[Cl-].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>[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:19]1[CH2:24][CH2:23][NH:22][CH:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:20]=1)(=[O:3])[CH3:2]

Komponenten

11

Edukt 7

HCID 10340Sodium CarbonateHCID 142176Phenyl triflimideHCID 433294Lithium ChlorideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 2724682Lithium diisopropylamideHCID 27343092-Acetylphenylboronic acidHCID 22266210Tert-butyl 4-[(trifluoromethyl)sulfonyloxy]-1,2,5,6-tetrahydropyridinecarboxylate

Produkt 1

HCID 22266253tert-Butyl 4-(2-acetylphenyl)-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-acetylphenylboronic acid (Aldrich) (1.63 g, 10 mmol), tert-butyl 4-[(trifluoromethyl)sulfonyloxy]-1,2,5,6-tetrahydropyridinecarboxylate [prepared by the method of Wustrow, D. J. and Wise, I. D. Synthesis, 1991, 993-995, from tert-butyl-4-oxopiperidine-1-carboxylate (Aldrich), LDA (Aldrich) and N-phenyltrifluoromethane-sulfonimide (Aldrich)) (3.64 g, 11 mmol), tetrakis(triphenylphosphine)palladium (0) (Strem Chemicals) (0.578 g, 0.5 mmol), LiCl (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 (1.77 g). MS (ESI, pos. ion) m/z: 302 (M+1); MS (ESI, neg. ion) m/z: 300 (M−1). Calc'd for C18H23NO3: 301.38.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-b4b1af8f0f534756a53286a2d8450290
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06977264B2

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