Potassium Carbonate → tert-Butyl (1-(pyridin-4-yl)piperidin-4-yl)methylcarbamate

HRID 1193302Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[NH:7]1[CH2:14][CH2:13][CH2:12][C@H:8]1[C:9](O)=O.BrC1C=CN=CC=1.[NH:22]1[CH2:27][CH2:26][CH:25]([CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:24][CH2:23]1>CS(C)=O.C(OCC)(=O)C.[Cl-].[Na+].[Cu]I>[N:7]1[CH:9]=[CH:8][C:12]([N:22]2[CH2:27][CH2:26][CH:25]([CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:34])([CH3:33])[CH3:35])[CH2:24][CH2:23]2)=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Potassium carbonate (3 eq), L-proline (0.4 eq), CuI (0.2 eq) and 4-bromopyridine (1 eq) were added under a protecting gas atmosphere to a solution of tert-butyl piperidin-4-ylmethyl-carbamate (3 g, 15 mmol) in DMSO. The reaction mixture was heated for 20 h at 100° C. After cooling to room temperature, the mixture was diluted with ethyl acetate and sat. sodium chloride solution and filtered over Celite, and the residue was then washed with ethyl acetate. The phases were separated, dried and concentrated under reduced pressure. The crude product was purified by column chromatography. Yield: 30%

Workup

temperatureAfter cooling to room temperature
filtrationfiltered over Celite
washthe residue was then washed with ethyl acetate
customThe phases were separated
customdried
concentrationconcentrated under reduced pressure
customThe crude product was purified by column chromatography

Sources & evidence

ORD record: ord-665ac254d1b84f6db03f0d61f23a579b
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680159B2

Reaction notes

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