Tetrahydrofuran → 1-(2-Tributylstannylmethoxyethyl)piperidine

HRID 642955Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 642955
[N:1]1([CH2:7]O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[O:9]1CCC[CH2:10]1.[H-].[Na+].[CH2:16]([Sn:20]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:21]I)[CH2:17][CH2:18][CH3:19]>C(OCC)(=O)C.O.CN(C)C=O>[CH2:16]([Sn:20]([CH2:21][O:9][CH2:10][CH2:7][N:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH2:25][CH3:26])[CH2:17][CH2:18][CH3:19]

Komponenten

8

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 446909Piperidin-1-ylmethanolHCID 10862926Tributyl(iodomethyl)stannane

Produkt 1

HCID 592597131-(2-Tributylstannylmethoxyethyl)piperidineAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 1-piperidinemethanol (1.3 g, 10 mmol) and tetrahydrofuran (30 ml) was added sodium hydride (60%, 418 mg, 10 mmol) at 0° C. (external temperature), followed by stirring at room temperature for 30 minutes. Then, to the reaction mixture was added dropwise a mixture of tributyl-iodomethyl-tin (3.0 g, 7.0 mmol), tetrahydrofuran (5 ml), and N,N-dimethylformamide (30 ml) at 0° C. Then, the reaction mixture was stirred at room temperature for 1 hour. To the reaction mixture were added water and ethyl acetate, and the organic layer was separated. The organic layer was sequentially washed with water and an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=20:1, NH silica gel) to obtain the title compound (2.1 g, 4.9 mmol, 70%).

Aufarbeitung

  1. additionThen, to the reaction mixture was added dropwise
  2. stirringThen, the reaction mixture was stirred at room temperature for 1 hour
  3. customthe organic layer was separated
  4. washThe organic layer was sequentially washed with water
  5. dry with materialan aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=20:1, NH silica gel)

Quellen und Nachweise

ORD-Eintrag
ord-5ab49a22196246278e41eb1f3ddff58e
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696347B2

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