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

HRID 530665ノート

反応式

HRID 530665 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-db8c87109fbe4d078a80c49f998a79e5
出典データセット
uspto-grants-2016_05
特許番号
US09353091B2

反応ノート

読み込み中…