Imidazole → Rac-cis-tert-butyl 4-[2-(2-iodoethyl)cyclopropyl]piperidine-1-carboxylate

HRID 1039049Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1039049
O[CH2:2][CH2:3][C@H:4]1[CH2:6][C@H:5]1[CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:39]I.N1C=CN=C1>ClCCl.C(OCC)C>[I:39][CH2:2][CH2:3][C@H:4]1[CH2:6][C@H:5]1[CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1

Komponenten

7

Edukt 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 66935269Cis tert-butyl 4-[2-(2-hydroxyethyl)cyclopropyl]piperidine-1-carboxylate

Produkt 1

HCID 67778116Rac-cis-tert-butyl 4-[2-(2-iodoethyl)cyclopropyl]piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

rac-cis-tert-butyl 4-[2-(2-hydroxyethyl)cyclopropyl]piperidine-1-carboxylate (100 mg, 0.37 mmol) from step 2 of this example was dissolved in dichloromethane (3.7 mL), triphenylphosphine (195 mg, 0.74 mmol), iodine (94 mg, 0.37 mmol) and imidazole (51 mg, 0.74 mmol) were added. After 20 minutes, diethyl ether (10 mL) was added, filtered through a silica gel pad (0.5 inch), concentrated and purified by column chromatography through a 24 gram AnaLogix™ silica gel cartridge eluting with 10% ethyl acetate/hexanes to give the title compound as a white solid.

Aufarbeitung

  1. filtrationfiltered through a silica gel pad (0.5 inch)
  2. concentrationconcentrated
  3. custompurified by column chromatography through a 24 gram AnaLogix™ silica gel cartridge
  4. washeluting with 10% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-d979ae6f2f3a4a7c8b9d5ebf07f60088
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552022B2

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