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Potassium hydride → (E)-3-[4-((S)-1-{2-[3,5-dimethyl-1-(tetrahydropyran-4-ylmethyl)-1H-pyrazol-4-yl]-ethyl}-pyrrolidin-2-yl)-phenyl]-acrylic acid methyl ester

HRID 549423
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 549423
[CH3:1][O:2][C:3](=[O:26])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([C@@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2[CH2:17][CH2:18][C:19]2[C:20]([CH3:25])=[N:21][NH:22][C:23]=2[CH3:24])=[CH:8][CH:7]=1.[H-].[K+].Br[CH2:30][CH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>O1CCCC1.CS(C)=O>[CH3:1][O:2][C:3](=[O:26])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[CH:8][C:9]([C@@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2[CH2:17][CH2:18][C:19]2[C:20]([CH3:25])=[N:21][N:22]([CH2:30][CH:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)[C:23]=2[CH3:24])=[CH:10][CH:11]=1
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Komponenten

5

Edukt 3

HCID 82127Potassium hydrideHCID 27732864-(Bromomethyl)oxaneHCID 57899243(E)-3-(4-{(S)-1-[2-(3,5-dimethyl-1H-pyrazol-4-yl)-ethyl]-pyrrolidin-2-yl}-phenyl)-acrylic acid methyl ester

Produkt 1

HCID 57899315(E)-3-[4-((S)-1-{2-[3,5-dimethyl-1-(tetrahydropyran-4-ylmethyl)-1H-pyrazol-4-yl]-ethyl}-pyrrolidin-2-yl)-phenyl]-acrylic acid methyl esterAusbeute 14,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21830753dimethylsulfoxide THFLösungsmittel

Versuchsvorschrift

To an ice cold mixture of (E)-3-(4-{(S)-1-[2-(3,5-dimethyl-1H-pyrazol-4-yl)-ethyl]-pyrrolidin-2-yl}-phenyl)-acrylic acid methyl ester (0.85 g, 2.4 mmol) and potassium hydride (115 mg, 2.88 mmol) in 4.0 mL tetrahydrofuran:dimethyl sulfoxide (9:1 v/v) was added 4-bromomethyltetrahydropyran (945 mg, 5.28 mmol). The mixture was slowly warmed to room temperature and stirred under nitrogen for 16 h. It was then quenched with aqueous ammonium chloride and added with ethyl acetate. The layers were separated and the organic layer was washed with more aqueous ammonium chloride. The aqueous layers were then washed with more ethyl acetate and the combined organic extracts were dried over magnesium sulfate and concentrated to a yellow oil. The oil was then purified via silica gel column chromatography (100:0 to 0:100 heptane:ethyl acetate) to give (E)-3-[4-((S)-1-{2-[3,5-dimethyl-1-(tetrahydro-pyran-4-ylmethyl)-1H-pyrazol-4-yl]-ethyl}-pyrrolidin-2-yl)-phenyl]-acrylic acid methyl ester (160 mg, 0.35 mmol, 14% yield) as a yellow oil. LC/MS (m/z): 452.5 (M+1).

Aufarbeitung

  1. customIt was then quenched with aqueous ammonium chloride
  2. additionadded with ethyl acetate
  3. customThe layers were separated
  4. washthe organic layer was washed with more aqueous ammonium chloride
  5. washThe aqueous layers were then washed with more ethyl acetate
  6. dry with materialthe combined organic extracts were dried over magnesium sulfate
  7. concentrationconcentrated to a yellow oil
  8. customThe oil was then purified via silica gel column chromatography (100:0 to 0:100 heptane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-483d324afebc4791a1783f0b5e9517c3
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07943652B2

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