Tert-butyl 4-cyanopiperidine-1-carboxylate → HCID 58896168, compound

HRID 2422356Notes

Reaction equation

C[Si](C)(C)N[Si](C)(C)C.[K].Cl[C:12]1[CH:17]=[CH:16][N:15]=[CH:14][C:13]=1[F:18].[C:19]([N:26]1[CH2:31][CH2:30][CH:29]([C:32]#[N:33])[CH2:28][CH2:27]1)([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]>C1(C)C=CC=CC=1>[C:22]([O:21][C:19]([N:26]1[CH2:31][CH2:30][C:29]([C:32]#[N:33])([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[F:18])[CH2:28][CH2:27]1)=[O:20])([CH3:25])([CH3:23])[CH3:24]

Participants

Conditions

Temperature: 80 °C

Procedure

Potassium hexamethyldisilazane (1.2 ml, 0.5 M solution in toluene) was slowly added to a solution of 4-chloro-3-fluoro-pyridin (0.5 g) and N-Boc-4-Cyano-Piperidine (0.312 g) in 1.5 ml toluene at room temperature, under nitrogen. The mixture was stirred at 80° C. for 2 hrs. After cooling, the reaction mixture was quenched in 1N HCl. The aqueous phase was extracted twice with toluene and the combined organic were dried over anhydrous magnesium sulfate and concentrated in vacuo. The crude product was purified by chromatography [SiO2; ethyl acetate-hexane (1:1)] to give 104 mg (90%) of 4-cyano-3′-fluoro-3,4,5,6-tetrahydro-2H-[4,4′]bipyridinyl-1-carboxylic acid tert-butyl ester; MS (ES+) 306 (M+H+).

Workup

temperatureAfter cooling
customthe reaction mixture was quenched in 1N HCl
extractionThe aqueous phase was extracted twice with toluene
dry with materialthe combined organic were dried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo
customThe crude product was purified by chromatography [SiO2; ethyl acetate-hexane (1:1)]

Sources & evidence

ORD record: ord-79775a8580664906b11d0c9637b1310e
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960401B2

Reaction notes

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