Water → (S)-1-(6-iodobenzo[d]thiazol-2-yl)pyrrolidin-3-ol

HRID 1691982Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1691982
[I:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]=[C:7](S(C)(=O)=O)[S:8][C:4]=2[CH:3]=1.[NH:15]1[CH2:19][CH2:18][C@H:17]([OH:20])[CH2:16]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[I:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]=[C:7]([N:15]3[CH2:19][CH2:18][C@H:17]([OH:20])[CH2:16]3)[S:8][C:4]=2[CH:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2733874(3S)-pyrrolidin-3-olHCID 669061396-Iodo-2-(methylsulfonyl)benzo[d]thiazole

Produkt 1

HCID 66905790(S)-1-(6-iodobenzo[d]thiazol-2-yl)pyrrolidin-3-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A stirred mixture of 6-iodo-2-(methylsulfonyl)benzo[d]thiazole (Reference Example 6c, 1.50 g, 4.42 mmol), (S)-pyrrolidin-3-ol (0.500 g, 5.74 mmol), and potassium carbonate (1.222 g, 8.84 mmol) in N,N-dimethylformamide (21.5 mL) was heated to 150° C. under microwave irradiation for 10 minutes. The reaction mixture was cooled to room temperature, then poured into water (350 mL) to give a precipitate. The precipitate was collected by filtration, rinsed with water, and then dissolved in ethyl acetate. The ethyl acetate solution was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure to give a crude solid that was purified by silica gel chromatography (100% CHCl3 to 97:3 CHCl3/methanol). Fractions containing product were combined an concentrated under reduced pressure to provide (S)-1-(6-iodobenzo[d]thiazol-2-yl)pyrrolidin-3-ol. 1H NMR (300 MHz, CD3OD) δ ppm 2.03-2.14 (m, 1H), 2.15-2.29 (m, 1H), 3.47-3.55 (m, 1H), 3.58-3.75 (m, 3H), 4.53-4.59 (m, 1H), 7.23 (d, J=8 Hz, 1H), 7.53-7.59 (m, 1H), 7.95-7.98 (m, 1H); MS (DCI/NH3) m/z 347 (M+H)+.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customto give a precipitate
  3. filtrationThe precipitate was collected by filtration
  4. washrinsed with water
  5. dissolutiondissolved in ethyl acetate
  6. dry with materialThe ethyl acetate solution was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customto give a crude solid that
  10. customwas purified by silica gel chromatography (100% CHCl3 to 97:3 CHCl3/methanol)
  11. additionFractions containing product
  12. concentrationan concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a79861fc52b84ae69db8f79db0196968
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153813B2

Notizen zur Reaktion

Wird geladen…