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Tetrabutylammonium Fluoride → [(3RS,4SR)-3-[(RS)-1-(5-Chloro-pyridin-2-yloxy)-2-hydroxy-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidin-1-yl]-(2-methyl-pyrimidin-5-yl)-methanone

HRID 906924
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 906924
C([Si](C)(C)[O:6][CH2:7][CH:8]([CH:17]1[CH:21]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=2)[CH2:20][N:19]([C:30]([C:32]2[CH:37]=C(C)N=[N:34][CH:33]=2)=[O:31])[CH2:18]1)[O:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=1)(C)(C)C.CC[CH2:43][CH2:44][N+:45](CCCC)(CCCC)CCCC.[F-]>C1COCC1.C(OCC)(=O)C>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([O:9][CH:8]([CH:17]2[CH:21]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=3)[CH2:20][N:19]([C:30]([C:32]3[CH:33]=[N:34][C:44]([CH3:43])=[N:45][CH:37]=3)=[O:31])[CH2:18]2)[CH2:7][OH:6])=[N:11][CH:12]=1
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Komponenten

5

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 67131606[(3RS,4SR)-3-[(RS)-2-(tert-butyl-dimethyl-silanyloxy)-1-(5-chloro-pyridin-2-yloxy)-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidin-1-yl]-(6-methyl-pyridazin-4-yl)-methanone

Produkt 1

HCID 67131690[(3RS,4SR)-3-[(RS)-1-(5-Chloro-pyridin-2-yloxy)-2-hydroxy-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidin-1-yl]-(2-methyl-pyrimidin-5-yl)-methanoneAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028
Tetrahydrofuran
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of [(3RS,4SR)-3-[(RS)-2-(tert-butyl-dimethyl-silanyloxy)-1-(5-chloro-pyridin-2-yloxy)-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidin-1-yl]-(6-methyl-pyridazin-4-yl)-methanone 0.024 g (0.038 mmol) dissolved in THF (4 mL) was added 0.05 mL of TBAF (1.0M in THF). The reaction mixture was stirred for 30 minutes at room temperature. The mixture was diluted with ethyl acetate and washed with water and aq. sodium bicarbonate solution subsequently. The separated organic phase was dried over sodium sulfate and concentrated in vaccuo after filtration. The residue was purified by TLC (SiO2, MeOH/DCM, 1:10) yielded 18 mg (93%) of the title compound as a light yellow oil. ES-MS m/e: 509.2 (M+H+).

Aufarbeitung

  1. washwashed with water and aq. sodium bicarbonate solution subsequently
  2. dry with materialThe separated organic phase was dried over sodium sulfate
  3. concentrationconcentrated in vaccuo
  4. filtrationafter filtration
  5. customThe residue was purified by TLC (SiO2, MeOH/DCM, 1:10)

Quellen und Nachweise

ORD-Eintrag
ord-56126ca93cec4b5d81d1717568b811fe
Quelldatensatz
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08012998B2

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