Cyclopentanone → Methyl 4-(N-cyclopentylamino)-3-iodobenzoate

HRID 1174637

Reaktionsgleichung

Reaktionsgleichung von HRID 1174637
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[I:12].[C:13]1(=O)[CH2:17][CH2:16][CH2:15][CH2:14]1.S([O-])([O-])(=O)=O.[Na+].[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(O)(=O)C>[CH:13]1([NH:1][C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=2[I:12])[CH2:17][CH2:16][CH2:15][CH2:14]1

Komponenten

7

Edukt 5

HCID 8452CyclopentanoneHCID 24436Sodium SulfateHCID 516892Sodium BicarbonateHCID 4104649Methyl 4-amino-3-iodobenzoateHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 21974264Methyl 4-(N-cyclopentylamino)-3-iodobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of methyl 4-amino-3-iodobenzoate from above (27.69 g, 100 mmol), cyclopentanone (52.8 mL, 600 mmol), and anhydrous sodium sulfate (1000 g, 142 mmol) in 500 mL of glacial acetic acid was stirred for two hours. Solid sodium triacetoxyborohydride (76.92, 345 mmol) was added in portions and stirred for 16 hrs at room temperature. The mixture was poured on to cool 900 mL of saturated aqueous sodium bicarbonate solution carefully and extracted with 150 mL (3×) of ethyl acetate. The ethyl acetate fraction was dried and evaporated. Purification with silica gel and 0.5% ethyl acetate in hexane gave 24 g (70%).

Aufarbeitung

  1. stirringstirred for 16 hrs at room temperature
  2. additionThe mixture was poured on
  3. extractionextracted with 150 mL (3×) of ethyl acetate
  4. dry with materialThe ethyl acetate fraction was dried
  5. customevaporated
  6. customPurification with silica gel and 0.5% ethyl acetate in hexane
  7. customgave 24 g (70%)

Quellen und Nachweise

ORD-Eintrag
ord-5a39de74bd9f4dce8c32bcdc576014c2
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07838537B2

Verknüpfte Notizen

Wird geladen…