Potassium Iodide → 2-Methyl-7-pyrrolidin-1-ylmethyl-3,7,8,9-tetrahydro-pyrano[3,2-e]indole-1-carboxylic Acid Benzyl Ester

HRID 966503

Reaktionsgleichung

Reaktionsgleichung von HRID 966503
[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:18]3[CH2:20][CH2:21][CH:22]([CH2:24]Br)[O:23][C:17]=3[CH:16]=[CH:15][C:14]=2[NH:13][C:12]=1[CH3:26])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-].[K+].[NH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1.C(OCC)(=O)C.CO.C(N(CC)CC)C>C(#N)C>[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:18]3[CH2:20][CH2:21][CH:22]([CH2:24][N:29]4[CH2:33][CH2:32][CH2:31][CH2:30]4)[O:23][C:17]=3[CH:16]=[CH:15][C:14]=2[NH:13][C:12]=1[CH3:26])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 31268PyrrolidineHCID 21980445Ethyl acetate methanol triethylamineHCID 233938867-Bromomethyl-2-methyl-3,7,8,9-tetrahydro-pyrano[3,2-e]indole-1-carboxylic acid benzyl ester

Produkt 1

HCID 233938872-Methyl-7-pyrrolidin-1-ylmethyl-3,7,8,9-tetrahydro-pyrano[3,2-e]indole-1-carboxylic Acid Benzyl EsterAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

7-Bromomethyl-2-methyl-3,7,8,9-tetrahydro-pyrano[3,2-e]indole-1-carboxylic acid benzyl ester (0.160 g, 0.390 mmol, 1 eq) was suspended in dry acetonitrile (10 mL) under Ar. Potassium iodide (catalytic) was added followed by the addition of pyrrolidine (0.125 mL, 1.50 mmol, 3.75 eq). The reaction mixture was stirred and heated to reflux. The reaction was followed by TLC (ethyl acetate/methanol/triethylamine 87/10/3). After 18 hours, the reaction was quenched with aqueous sodium bicarbonate and extracted with ethyl acetate (3×). The combined organic extracts were washed with brine and dried over Na2SO4. After removing the solvent, the residue was loaded on silica gel and chromatographed, eluting with ethyl acetate /methanol/triethylamine 87/10/3. 0.063 g (40% yield) of the indole-pyrrolidine was obtained as a white solid. This was converted to the .HCl salt, LC/MS (ESI+) 405 (M+1), Anal. (C25H28N2O3.HCl.0.2 DMF) C, H, N.

Aufarbeitung

  1. temperatureheated to reflux
  2. customthe reaction was quenched with aqueous sodium bicarbonate
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. customAfter removing the solvent
  7. customchromatographed
  8. washeluting with ethyl acetate /methanol/triethylamine 87/10/3

Quellen und Nachweise

ORD-Eintrag
ord-5e615d1095cd4124b49f917df5933713
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06951848B2

Verknüpfte Notizen

Wird geladen…