Diisopropylethylamine → Methyl 4-(1-methoxycarbonylpyrrolidin-3-yl)benzoate

HRID 1061026노트

반응식

HRID 1061026 반응식
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)(=O)=O.[CH3:19][O:20][C:21]([N:23]1[CH2:27][CH:26]=[CH:25][CH2:24]1)=[O:22].[Cl-].[Li+].O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.C(N(C(C)C)CC)(C)C>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:19][O:20][C:21]([N:23]1[CH2:27][CH2:26][CH:25]([C:7]2[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=2)[CH2:24]1)=[O:22]

참가 물질

8

반응물 5

HCID 81531DiisopropylethylamineHCID 433294Lithium ChlorideHCID 521585Tris(furan-2-yl)phosphaneHCID 8199331-Methoxycarbonyl-3-pyrrolineHCID 5315090Methyl 4-(((trifluoromethyl)sulfonyl)oxy)benzoate

생성물 1

HCID 22710505Methyl 4-(1-methoxycarbonylpyrrolidin-3-yl)benzoate

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

In N,N-dimethylformamide (25 ml), methyl 4-trifluoromethanesulfonyloxybenzoate (1.05 g), 1-methoxycarbonyl-3-pyrroline (1.0 g), lithium chloride (0.51 g), palladium (II) acetate(53 mg) and tri(2-furyl)phosphine (100 mg) were dissolved, followed by the addition of diisopropylethylamine (2.8 ml). Under an argon gas atmosphere, the resulting mixture was stirred at 90° C. for 11 hours and then, at 100° C. for 7 hours. The residue obtained by distilling off the solvent under reduced pressure was added with dichloromethane and water. The organic layer so separated was washed with water and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=9:1˜5:1). The purified product was dissolved in methanol (30 ml), followed by the addition of 10% palladium carbon (water content: about 50%, 186 mg) and ammonium formate (197 mg). The resulting mixture was heated under reflux for 2 hours. After the removal of the catalyst by filtration, the solvent was distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column (10% ethyl acetate-toluene), whereby the title compound (241 mg, 25%) was obtained.

후처리

  1. waitat 100° C. for 7 hours
  2. customThe residue obtained
  3. distillationby distilling off the solvent under reduced pressure
  4. additionwas added with dichloromethane and water
  5. customThe organic layer so separated
  6. washwas washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was then distilled off under reduced pressure
  9. customThe residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=9:1˜5:1)
  10. dissolutionThe purified product was dissolved in methanol (30 ml)
  11. additionfollowed by the addition of 10% palladium carbon (water content: about 50%, 186 mg) and ammonium formate (197 mg)
  12. temperatureThe resulting mixture was heated
  13. temperatureunder reflux for 2 hours
  14. customAfter the removal of the catalyst
  15. filtrationby filtration
  16. distillationthe solvent was distilled off under reduced pressure
  17. customThe residue was purified by chromatography on a silica gel column (10% ethyl acetate-toluene), whereby the title compound (241 mg, 25%)
  18. customwas obtained

출처 및 근거

ORD 기록
ord-4da9812d83a54d09919fdd3bf9736d2d
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06525042B1

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