N,N,N',N'-Tetramethylethylenediamine → Tert-butyl 1'-(6-cyanopyrazin-2-yl)-4,4'-bipiperidine-1-carboxylate

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Reaktionsgleichung

CS(C1C=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][CH:14]([CH:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)[CH2:13][CH2:12]2)=CC=1)(=O)=O.C[N:31](C)[CH2:32][CH2:33][N:34](C)C.C1(P(C2C=CC=CC=2)CCCCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C-:69]#[N:70].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[C:69]([C:32]1[N:31]=[C:8]([N:11]2[CH2:16][CH2:15][CH:14]([CH:17]3[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:28])([CH3:29])[CH3:27])=[O:24])[CH2:21][CH2:22]3)[CH2:13][CH2:12]2)[CH:9]=[N:34][CH:33]=1)#[N:70]

Komponenten

Reaktionsbedingungen

Temperatur: 160 °C

Versuchsvorschrift

The tert-butyl 1′-[4-(methylsulfonyl)phenyl]-4,4′-bipiperidine-1-carboxylate (500 mg, 1.3 mmol), palladium(II) acetate (6 mg, 0.026 mmol), N,N,N′,N′-tetramethylethylenediamine (0.15 mL, 0.26 mmol), 1,5-bis(diphenylphosphino)pentane, potassium cyanide (93 mg, 1.43 mmol) were add in a seal bottle with 13 mL anhydrous toluene. The mixture was degassed by N2 and closed and heated to 160° C. overnight (16 h). The reaction was cooled down to r.t. and diluted with ethyl acetate 50 mL, filtered through celite, and concentrated on rotavapor. The crude material was purified by silica gel flash chromatography with 30% acetone: hexane to yield the title compound.

Aufarbeitung

customThe mixture was degassed by N2
customclosed
temperatureThe reaction was cooled down to r.t.
additiondiluted with ethyl acetate 50 mL
filtrationfiltered through celite
concentrationconcentrated on rotavapor
customThe crude material was purified by silica gel flash chromatography with 30% acetone

Quellen und Nachweise

ORD-Eintrag: ord-223fed778c3f45a087c65bd0e6f2c262
Quelldatensatz: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08399485B2

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