Imidazole → tert-butyl-4-[(1R,2R)-2-(iodomethyl)cyclopropyl]piperidine-1-carboxylate

HRID 1468823Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1468823
O[CH2:2][C@@H:3]1[CH2:5][C@@H:4]1[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.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N1C=CN=C1.[I:43]I>C1COCC1>[C:15]([O:14][C:12]([N:9]1[CH2:10][CH2:11][CH:6]([C@H:4]2[CH2:5][C@H:3]2[CH2:2][I:43])[CH2:7][CH2:8]1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 53393314HCID 53393314, Verbindung

Produkt 1

HCID 86717780tert-butyl-4-[(1R,2R)-2-(iodomethyl)cyclopropyl]piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Intermediate 4 (2.0 g, 7.8 mmol), PPh3 (2.68 g, 10.2 mmol), imidazole (1.07 g, 15.7 mmol), and iodine (2.98 g, 11.7 mmol) were dissolved in THF (15 mL), and the resulting solution was stirred at RT for 2 h. The solution was quenched with sat. Na2S2O3, and extracted with Et2O. The organic layer was dried over Na2SO4, filtered, and concentrated. The residue was purified by silica gel column chromatography (10/1 hexanes/EtOAc) which provided the title compound.

Aufarbeitung

  1. customThe solution was quenched with sat. Na2S2O3
  2. extractionextracted with Et2O
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (10/1 hexanes/EtOAc) which

Quellen und Nachweise

ORD-Eintrag
ord-f50b51ae79fe44209a2b7e8ea6d90f59
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006228B2

Notizen zur Reaktion

Wird geladen…