Acetic Acid → HCID 68951075, Verbindung

HRID 2384931Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2384931
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:14][CH2:13][NH:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[C:15](O)(=O)C.C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11]2)=[O:9])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68953107HCID 68953107, Verbindung

Produkt 1

HCID 68951075HCID 68951075, VerbindungAusbeute 68,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution (4-bromo-phenyl)-pyrrolidin-3-yl-methanone (2.24 g, 8.81 mmol) in methanol (44 mL), add acetic acid (1.01 mL, 17.6 mmol) and formaldehyde (2.15 g, 26.4 mmol, 37% aqueous solution). After 15 min, add sodium triacetoxyborohydride (5.60 g, 26.4 mmol) and allow the mixture to stir at RT for one hour. Concentrate the reaction mixture. Add water and adjust the solution to pH=10 with 2 N NaOH. Extract the aqueous with ethylacetate. Dry the combined organic layers over Na2SO4, filter, and concentrate. Purify the crude material by flash chromatography, eluting with 5-10% MeOH (2N NH3)/CH2Cl2 to give 1.61 g (68%) of the title compound. LC-MS/ES m/z (79Br) 268.0 [M+H]+.

Aufarbeitung

  1. concentrationConcentrate the reaction mixture
  2. extractionExtract the aqueous with ethylacetate
  3. dry with materialDry the combined organic layers over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the crude material by flash chromatography
  7. washeluting with 5-10% MeOH (2N NH3)/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-240f835fc26849b18f937084b70199d9
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263772B2

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