Sodium hydride → 2-Oxo-[1,4']bipiperidinyl-1'-carboxylic acid benzyl ester

HRID 2221075Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2221075
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18](=[O:24])[CH2:19][CH2:20][CH2:21][CH2:22]Cl)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+]>O1CCCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][C:18]2=[O:24])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 24758Sodium hydrideHCID 233699784-(5-Chloro-pentanoylamino)-piperidine-1-carboxylic acid benzyl ester

Produkt 1

HCID 233699802-Oxo-[1,4']bipiperidinyl-1'-carboxylic acid benzyl esterAusbeute 107,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-(5-Chloro-pentanoylamino)-piperidine-1-carboxylic acid benzyl ester (15.6 g) was added to a suspension of sodium hydride (2.12 g) in tetrahydrofuran (175 mL). After being stirred overnight, the reaction was quenched with water, then the tetrahydrofuran was removed under reduced pressure. The aqueous solution was diluted with water and extracted with methylene chloride (4×50 mL). The organic extracts were dried and evaporated to give the title compound (15 g). Rf=0.30 in ethyl acetate. MS: m/z=317 (M+H).

Aufarbeitung

  1. customthe reaction was quenched with water
  2. customthe tetrahydrofuran was removed under reduced pressure
  3. additionThe aqueous solution was diluted with water
  4. extractionextracted with methylene chloride (4×50 mL)
  5. customThe organic extracts were dried
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-51c6e232feac4beea4414fbd8faa7030
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07368461B2

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