Phosphoric Acid → Tert-butyl 4-[4,5-diiodo-1-(2-pyrrolidin-1-ylethyl)imidazol-2-yl]piperidine-1-carboxylate

HRID 2088918Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2088918
[OH-].[K+].[I:3][C:4]1[N:5]=[C:6]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[NH:7][C:8]=1[I:9].Cl.Cl[CH2:25][CH2:26][N:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1.P(=O)(O)(O)O>CN1CCCC1=O.O>[I:3][C:4]1[N:5]=[C:6]([CH:10]2[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15]2)[N:7]([CH2:25][CH2:26][N:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)[C:8]=1[I:9]

Komponenten

7

Edukt 4

HCID 1004Phosphoric AcidHCID 14797Potassium HydroxideHCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 67112091tert-butyl 4-(4,5-diiodo-1H-imidazol-2-yl)piperidine-1-carboxylate

Produkt 1

HCID 67112102Tert-butyl 4-[4,5-diiodo-1-(2-pyrrolidin-1-ylethyl)imidazol-2-yl]piperidine-1-carboxylateAusbeute 99,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

Add potassium hydroxide (45.13 g, 4.0 eq) to a solution of tert-butyl 4-(4,5-diiodo-1H-imidazol-2-yl)piperidine-1-carboxylate (86 g, 170.9 mmol) in N-methylpyrrolidinone (258 mL) portionwise over 25 minutes, maintaining the temperature below 40° C. Stir the mixture for 25 minutes, then add 1-(2-chloroethyl)pyrrolidine hydrochloride (47.5 g, 1.6 eq) portionwise. Stir the resulting mixture for 16 hours at 40° C., then allow to cool to room temperature. Pour the reaction into water (3.1 L) and add aqueous 15% phosphoric acid to adjust the pH to 7.5-8. Stir the resulting suspension for one hour at 0-5° C. Filter, wash with water, and dry under vacuum at 50° C. to give tert-butyl 4-[4,5-diiodo-1-(2-pyrrolidin-1-ylethyl)imidazol-2-yl]piperidine-1-carboxylate (102 g, 99%). MS (ES) m/z=601 [M]+.

Aufarbeitung

  1. temperaturemaintaining the temperature below 40° C
  2. stirringStir the resulting mixture for 16 hours at 40° C.
  3. additionPour
  4. stirringStir the resulting suspension for one hour at 0-5° C
  5. filtrationFilter
  6. washwash with water
  7. customdry under vacuum at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-11b17d9324424668b6b7a63336a18302
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436002B2

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