Potassium Carbonate → Isopropyl 4-(2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate

HRID 1676162Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.CS(O[CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][CH:23]([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O.O>[O:8]=[C:4]1[CH:3]=[C:2]([O:1][CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][CH:23]([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[CH:7]=[CH:6][NH:5]1

Participants

Conditions

Temperature: 140 °C

Procedure

A stirring mixture of 4-hydroxypyridin-2(1H)-one (1.5 g, 13.5 mmol), isopropyl 4-(methylsulfonyloxy)piperidine-1-carboxylate (5.0 g, 18.9 mmol, prepared according to the procedure described in Step C of Example 1) and potassium carbonate (3.7 g, 27.0 mmol, EMD) in DMF (80 mL) was heated at 140° C. for 2 h and then cooled to room temperature. The resulting mixture was diluted with EtOAc and H2O and the aqueous layer was extracted further with EtOAc (7×). The combined extracts were washed with saturated NH4Cl aqueous solution (2×), dried (Na2SO4) and evaporated. The residual was purified by flash chromatography (0 to 100% EtOAc/Hexanes and then 5% MeOH/CH2Cl2) to yield 1.67 g (44%) of the product as an off-white solid. MS (ESI) 281 (M+H).

Workup

customprepared
temperaturecooled to room temperature
extractionthe aqueous layer was extracted further with EtOAc (7×)
washThe combined extracts were washed with saturated NH4Cl aqueous solution (2×)
dry with materialdried (Na2SO4)
customevaporated
customThe residual was purified by flash chromatography (0 to 100% EtOAc/Hexanes

Sources & evidence

ORD record: ord-9d66c0858ef04b13b3a19bc4ca7f4530
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003796B2

Reaction notes

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