1,3-Propanediol → 3-[3-(5-Isoquinolinylsulfonyloxy)-5-methylphenoxy]propanol

HRID 442968Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 442968
[CH:1]1[C:10]2[C:5](=[C:6]([S:11]([O:14][C:15]3[CH:16]=[C:17]([OH:22])[CH:18]=[C:19]([CH3:21])[CH:20]=3)(=[O:13])=[O:12])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.C(P(CCCC)CCCC)CCC.[CH2:36](O)[CH2:37][CH2:38][OH:39].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1.CCCCCC>[CH:1]1[C:10]2[C:5](=[C:6]([S:11]([O:14][C:15]3[CH:16]=[C:17]([CH:18]=[C:19]([CH3:21])[CH:20]=3)[O:22][CH2:36][CH2:37][CH2:38][OH:39])(=[O:12])=[O:13])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Komponenten

7

Edukt 4

HCID 104421,3-PropanediolHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 227225063-(5-Isoquinolinylsulfonyloxy)-5-methylphenol

Produkt 1

HCID 227225083-[3-(5-Isoquinolinylsulfonyloxy)-5-methylphenoxy]propanolAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a solution of 3-(5-isoquinolinylsulfonyloxy)-5-methylphenol (630 mg, 2.0 mmol), as prepared in the preceding step, tri-n-butylphosphine (607 mg, 3.0 mmol) and 1,3-propanediol (760 mg, 10 mmol) in anhydrous tetrahydrofuran (20 mL) was added 1,1'-(azodicarbonyl)dipiperidine (757 mg, 3.0 mmol). The mixture was stirred at ambient temperature overnight. Hexane (30 mL) was added to the mixture and the precipitates were removed by filtration. The filtrate was evaporated in vacuo, and the residue was purified by flash column chromatography (4:1 ethyl acetate/dichloromethane) to give the title compound as a colorless oil (620 mg, 82%). 1H-NMR (300 MHz, CDCl3) δ 9.41 (s, 1H), 8.80 (d, J=6.1 Hz, 1H), 8.54 (d, J=6.1 Hz, 1H), 8.33 (d, J=7.2 Hz, 1H), 8.29 (d, J=7.6 Hz, 1H), 7.67 (t, J=7.7 Hz, 1H), 6.56 (s, 1H), 6.29 (s, 1H), 6.24 (s, 1H), 3.89 (t, J=6.1 Hz, 2H), 3.75 (t, J=6.0 Hz, 2H), 2.16 (s, 3H), 2.05 (m, 2H), 1.90 (br s, 1H).

Aufarbeitung

  1. customthe precipitates were removed by filtration
  2. customThe filtrate was evaporated in vacuo
  3. customthe residue was purified by flash column chromatography (4:1 ethyl acetate/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-a4c93ff9a10149268eeab9cafd95cf8e
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05891909

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