2-Pyrrolidone → 1-(3-Tert-butyl-5-iodo-4-methoxyphenyl)pyrrolidin-2-one

HRID 530665노트

반응식

HRID 530665 반응식
[C:1]([C:5]1[CH:10]=[C:9](I)[CH:8]=[C:7]([I:12])[C:6]=1[O:13][CH3:14])([CH3:4])([CH3:3])[CH3:2].[NH:15]1[CH2:19][CH2:18][CH2:17][C:16]1=[O:20].P([O-])([O-])([O-])=O.[K+].[K+].[K+].N[C@@H]1CCCC[C@H]1N>O1CCOCC1.[Cu]I>[C:1]([C:5]1[CH:10]=[C:9]([N:15]2[CH2:19][CH2:18][CH2:17][C:16]2=[O:20])[CH:8]=[C:7]([I:12])[C:6]=1[O:13][CH3:14])([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 120252-PyrrolidoneHCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 574194401-(Tert-butyl)-3,5-diiodo-2-methoxybenzene

생성물 1

HCID 666999841-(3-Tert-butyl-5-iodo-4-methoxyphenyl)pyrrolidin-2-one

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 312751,4-Dioxane용매

반응 조건

온도
110 °C

실험 절차

In a 5 mL microwave tube under N2 flush were added 1-tert-butyl-3,5-diiodo-2-methoxybenzene (208 mg, 0.5 mmol), 2-pyrrolidone (0.092 mL, 1.200 mmol), potassium phosphate (223 mg, 1.050 mmol), (+/−)-trans-1,2-diaminocyclohexane (0.012 mL, 0.100 mmol) and copper(I) iodide (2.381 mg, 0.013 mmol) in dioxane (2 mL). The tube was sealed, sparged with N2 for 10 minutes, heated by microwave irradiation at 110° C. for 1 hour, cooled and partitioned between ethyl acetate and water adjusting the pH to 1 with HCl. The aqueous layer was extracted with ethyl acetate. The organics were combined, washed with H2O, and brine. The organic was dried (Na2SO4), filtered, and stirred for 0.5 hours with 3-mercaptopropyl functionalized silica, filtered and concentrated. The crude product was purified on an Isco 12 g silica cartridge eluting with 4:1 hexane/ethyl acetate to give the title compound.

후처리

  1. customIn a 5 mL microwave tube under N2 flush
  2. customThe tube was sealed
  3. customsparged with N2 for 10 minutes
  4. temperaturecooled
  5. custompartitioned between ethyl acetate and water adjusting the pH to 1 with HCl
  6. extractionThe aqueous layer was extracted with ethyl acetate
  7. washwashed with H2O, and brine
  8. dry with materialThe organic was dried (Na2SO4)
  9. filtrationfiltered
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe crude product was purified on an Isco 12 g silica cartridge
  13. washeluting with 4:1 hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-db8c87109fbe4d078a80c49f998a79e5
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09353091B2

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