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

HRID 1676162노트

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HRID 1676162 반응식
[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

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 546960044-Hydroxy-2(1H)-pyridinoneHCID 59158905Isopropyl 4-(methylsulfonyloxy)piperidine-1-carboxylate

생성물 1

HCID 67367983Isopropyl 4-(2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate수율 44%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
140 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-9d66c0858ef04b13b3a19bc4ca7f4530
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003796B2

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