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Piperidine → HCID 58981682, Verbindung

HRID 1182074
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1182074
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][CH2:11][CH2:12][O:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])=[CH:5][CH:4]=1)=O.[NH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(Cl)Cl.C(O)(=O)C>[N:24]1([CH2:1][C:3]2[CH:8]=[CH:7][C:6]([C:9]#[C:10][CH2:11][CH2:12][O:13][S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)(=[O:16])=[O:15])=[CH:5][CH:4]=2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8082PiperidineHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 44243538HCID 44243538, Verbindung

Produkt 1

HCID 58981682HCID 58981682, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176
Acetic Acid
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of the product of Example 8 (2.0 g), piperidine (0.91 mL), and acetic acid (0.42 mL) in DCM (100 mL) was treated with sodium triacetoxyborohydride (1.95 g) at room temperature. After 16 h, the resulting mixture was treated with 10% aqueous sodium hydroxide (30 mL). The aqueous phase was extracted with DCM (2×300 mL). The combined organic phases were dried (magnesium sulfate) and concentrated under reduced pressure. The residue was diluted in DCM (100 mL) and passed through a pad of silica gel. The pad was washed with DCM (3×200 mL). The combined filtrate was concentrated under reduced pressure, giving the title compound as a brown oil (2.3 g).

Aufarbeitung

  1. extractionThe aqueous phase was extracted with DCM (2×300 mL)
  2. dry with materialThe combined organic phases were dried (magnesium sulfate)
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was diluted in DCM (100 mL)
  5. washThe pad was washed with DCM (3×200 mL)
  6. concentrationThe combined filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-06f9ccbffbd748bc99a843f8523027e3
Quelldatensatz
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07288540B2

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