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

HRID 1518444ノート

反応式

HRID 1518444 の反応式
[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

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 546960044-Hydroxy-2(1H)-pyridinone

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-91f151dacfa54c258d3517d1190ae0ba
出典データセット
uspto-grants-2012_07
特許番号
US08232404B2

反応ノート

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