Imidazole → Tert-butyl 4-(2-iodoethyl)piperidine-1-carboxylate

HRID 278232

Reaktionsgleichung

Reaktionsgleichung von HRID 278232
O[CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:41]I.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(#N)C.CCOCC.[Cl-].[Na+].O.[O-]S([O-])(=O)=O.[Cu+2]>[I:41][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1

Komponenten

10

Edukt 5

HCID 795ImidazoleHCID 807Iodine2×HCID 11776TriphenylphosphineHCID 24477Sodium ThiosulfateHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidine

Produkt 1

HCID 9974426Tert-butyl 4-(2-iodoethyl)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24462Copper SulfateKatalysatorHCID 3283Diethyl EtherLösungsmittel2×HCID 6342AcetonitrileLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Combined 4-(2-hydroxyeth-1-yl)-1-tert-butoxylcarbonylpiperidine (37.4 g, 0.16 mol, from Step B), triphenylphosphine (55 g, 0.21 mol) and imidazole (14 g, 0.21 mol) in 800 mL of 33% acetonitrile in ether. Cooled to 0° C. and added iodine (56 g, 0.22 mol) portionwise. The iodine is de-colored until the endpoint of the reaction. Diluted with 1 L of ether. Washed organic layer with 2×500 mL each of sat'd. aq. Na2S2O3, sat. aq. CuSO4 and brine. Dried over magnesium sulfate, filtered and concentrated. Triphenylphosphine oxide precipitates. Added ether and filtered the slurry through a plug of silica gel. Purified a portion of the crude material by flash chromatography (5% ethyl acetate in hexane eluent) to afford the title compound.

Aufarbeitung

  1. dry with materialDried over magnesium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customTriphenylphosphine oxide precipitates
  5. filtrationAdded ether and filtered the slurry through a plug of silica gel
  6. customPurified a portion of the crude material by flash chromatography (5% ethyl acetate in hexane eluent)

Quellen und Nachweise

ORD-Eintrag
ord-c83c962e4a924518a69d95c326d2625c
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06358979B1

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