tert-Butanol → 1-[6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]ethane-1,2-diol

HRID 1881969Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1881969
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:21]3[NH:25][C:24]([C:26]4[CH:31]=[CH:30]C(C=C)=[CH:28][N:27]=4)=[CH:23][CH:22]=3)[CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[C:34]([OH:38])(C)([CH3:36])[CH3:35].CC[C@H]1[C@H]2C[C@H]([C@H](OC3C4C(=CC=CC=4)C(O[C@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C([O:60]C)C=C4)N(CC2)C1.S([O-])([O-])=O.[Na+].[Na+]>C(OC)(=O)C.O>[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:21]3[NH:25][C:24]([C:26]4[N:27]=[CH:28][C:35]([CH:34]([OH:38])[CH2:36][OH:60])=[CH:30][CH:31]=4)=[CH:23][CH:22]=3)[CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Komponenten

7

Edukt 4

HCID 6386tert-ButanolHCID 24437Sodium SulfiteHCID 510036741-((1R)-((2R,4R,5S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)-4-((1R)-((2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazineHCID 593314472-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-5-ethenylpyridine

Produkt 1

HCID 251070761-[6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]ethane-1,2-diolAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6584Methyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-5-ethenylpyridine (110 mg) in a mixed solvent of tert-butyl alcohol (1.5 mL) and water (1.5 mL) was added AD-mix-α (350 mg; Aldrich), and the mixture was stirred under ice-cooling for 4 hr. Sodium sulfite (30 mg) was added and the mixture was stirred for 30 min. The reaction mixture was diluted with methyl acetate, washed with water and saturated brine, dried (MgSO4) and concentrated. The residue was subjected to preparative HPLC to give the title compound (47 mg, yield 40%) as a yellow amorphous solid. MS: 497 (MH+).

Aufarbeitung

  1. temperaturecooling for 4 hr
  2. stirringthe mixture was stirred for 30 min
  3. washwashed with water and saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d25bd9bfaa8f4a1785b13c3cef677368
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318746B2

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