Trifluoroacetic acid → 4-(5-Chloro-isoquinolin-6-yloxy)-cyclohexanone

HRID 2370736ノート

反応式

HRID 2370736 の反応式
[Cl:1][C:2]1[C:11]([O:12][CH:13]2[CH2:22][CH2:21][C:16]3(OCC[O:17]3)[CH2:15][CH2:14]2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.C(O)(C(F)(F)F)=O>C1COCC1.O.ClCCl.O.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[C:11]([O:12][CH:13]2[CH2:14][CH2:15][C:16](=[O:17])[CH2:21][CH2:22]2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2

参加物

7

反応物 2

HCID 6422Trifluoroacetic acid4 回HCID 592685835-Chloro-6-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-isoquinoline

生成物 1

HCID 592685134-(5-Chloro-isoquinolin-6-yloxy)-cyclohexanone

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 516892Sodium Bicarbonate溶媒HCID 21881883Oxolane--water (1/1)溶媒

実験手順

549 mg (1.72 mmol) 5-Chloro-6-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-isoquinoline (78) were dissolved in 20 ml THF/H2O (3:1). 1 ml TFA was added and the mixture was stirred at room temperature. After 1 h, 2 ml TFA were added and the temperature was increased to 50° C. After 5 d at 50° C., 2 ml TFA were added. After one additional day, 2 ml TFA were added and the temperature was increased to 100° C. After 5 h, the reaction was allowed to cool down to room temperature and the mixture was diluted with dichloromethane and H2O, Solid NaHCO3 was added for neutralization. The phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic layers were dried over MgSO4 and evaporated. After final purification by preparative HPLC, 533 mg of the title compound as trifluoroacetate were obtained. Rt=0.88 min (Method #4). Detected mass: 276.2/278.2 (M+H+).

後処理

  1. temperaturethe temperature was increased to 50° C
  2. waitAfter 5 d at 50° C.
  3. temperaturethe temperature was increased to 100° C
  4. waitAfter 5 h
  5. temperatureto cool down to room temperature
  6. additionwas added for neutralization
  7. customThe phases were separated
  8. extractionthe aqueous phase was extracted with dichloromethane
  9. dry with materialThe combined organic layers were dried over MgSO4
  10. customevaporated
  11. customAfter final purification by preparative HPLC, 533 mg of the title compound as trifluoroacetate
  12. customwere obtained

出典と根拠

ORDレコード
ord-9bfe03d7e1e64b2395020c9e843376e3
出典データセット
uspto-grants-2014_04
特許番号
US08710228B2

反応ノート

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