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Lithium borohydride → 1-(benzo[d][1,3]dioxol-5-yl)-N-(3-bromo-4-(hydroxymethyl)phenyl)cyclopropanecarboxamide

HRID 1665736
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1665736
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:15][C:16]4[CH:25]=[CH:24][C:19]([C:20](OC)=[O:21])=[C:18]([Br:26])[CH:17]=4)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.[Li+].[BH4-]>C1COCC1.CCOCC.O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:15][C:16]4[CH:25]=[CH:24][C:19]([CH2:20][OH:21])=[C:18]([Br:26])[CH:17]=4)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1
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Komponenten

4

Edukt 2

HCID 4148881Lithium borohydrideHCID 59207086Methyl 4-(1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-2-bromobenzoate

Produkt 1

HCID 592062471-(benzo[d][1,3]dioxol-5-yl)-N-(3-bromo-4-(hydroxymethyl)phenyl)cyclopropanecarboxamideAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 70417672THF ether H2OLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

Methyl 4-(1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-2-bromobenzoate (4.12 g, 9.9 mmol) was added to a solution of LiBH4 (429 mg, 19.8 mmol) in THF/ether/H2O (20/20/1 mL) and was allowed to stir at 25° C. After 16 hours, the reaction was quenched with H2O (10 mL). The reaction mixture was diluted with dichloromethane (25 mL) and was extracted with 1N HCl (30 mL×3) and brine (30 mL). The organic extracts were dried over Na2SO4 and evaporated. The crude product was purified by chromatography on silica gel (eluting with 0-100% ethyl acetate in hexanes) to afford 1-(benzo[d][1,3]dioxol-5-yl)-N-(3-bromo-4-(hydroxymethyl)phenyl)cyclopropanecarboxamide (2.84 g, 74%). ESI-MS m/z calc. 389.0, found 390.1 (M+1)+; retention time 2.91 minutes.

Aufarbeitung

  1. customthe reaction was quenched with H2O (10 mL)
  2. additionThe reaction mixture was diluted with dichloromethane (25 mL)
  3. extractionwas extracted with 1N HCl (30 mL×3) and brine (30 mL)
  4. dry with materialThe organic extracts were dried over Na2SO4
  5. customevaporated
  6. customThe crude product was purified by chromatography on silica gel (eluting with 0-100% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-ecf7222cd7b4483a97c72a0cb6e5cdf0
Quelldatensatz
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08039491B2

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