Acetone → Tert-butyl 4-(iodomethyl)piperidine-1-carboxylate

HRID 1862671Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1862671
CS(O[CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)(=O)=O.[I-:19].[Na+].[CH3:21]C(C)=O>>[C:15]([O:14][C:12]([N:9]1[CH2:10][CH2:11][CH:6]([CH2:21][I:19])[CH2:7][CH2:8]1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

Komponenten

4

Edukt 3

HCID 180AcetoneHCID 5238Sodium IodideHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

Produkt 1

HCID 10448961Tert-butyl 4-(iodomethyl)piperidine-1-carboxylate

Versuchsvorschrift

A mixture of 1-(t-butoxycarbonyl)piperidin-4-yl methanesulfonate (13.58 g, 46.4 mmol) and sodium iodide (34.68 g, 232 mmol) in acetone (80 mL) was heated to reflux for 3 h. The mixture was partitioned between ether (350 mL) and water (350 mL). The organic layer was washed with saturated aq. brine (250 mL), and the aqueous layers were extracted in succession with ether (250 mL). The combined organic layers were dried (sodium sulfate), decanted, and evaporated to give the title compound (14.8 g) as a pale yellow oil.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. customThe mixture was partitioned between ether (350 mL) and water (350 mL)
  4. washThe organic layer was washed with saturated aq. brine (250 mL)
  5. extractionthe aqueous layers were extracted in succession with ether (250 mL)
  6. dry with materialThe combined organic layers were dried (sodium sulfate)
  7. customdecanted
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-04a02a1c97374df3b14d6c5b108b2f3d
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06538002B1

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