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

HRID 1518444노트

반응식

HRID 1518444 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][C:23]([CH3:26])([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][C:23]([CH3:26])([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 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 546960044-Hydroxy-2(1H)-pyridinone

생성물 1

HCID 67366878Tert-butyl 4-(2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate수율 38.7%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
90 °C

실험 절차

A stirring mixture of 4-hydroxypyridin-2(1H)-one (1.2 g, 10 8 mmol, prepared according to the procedure described at Step A of Example 8), tert-butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate (4.83 g, 17 3 mmol, prepared according to the procedure described at Step C of Example 1) and potassium carbonate (3.13 g, 22 7 mmol) in DMF (45 mL) was heated at 90° C. for 14 hrs and then cooled to room temperature. The resulting mixture was diluted with EtOAc and H2O and the aqueous layer was extracted further with EtOAc (5×). The combined extracts were washed with brine, dried (Na2SO4) and evaporated under reduced pressure. The residual was purified by flash chromatography on silica gel (0 to 10% MeOH/CH2Cl2) to yield 1.23 g (38.7%) of the product as a pinkish solid. MS (ESI) 295 (M+H).

후처리

  1. customprepared
  2. customprepared
  3. temperaturecooled to room temperature
  4. extractionthe aqueous layer was extracted further with EtOAc (5×)
  5. washThe combined extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated under reduced pressure
  8. customThe residual was purified by flash chromatography on silica gel (0 to 10% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-91f151dacfa54c258d3517d1190ae0ba
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08232404B2

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