Benzyl chloroformate → benzyl 4-(4-((tetrahydro-2H-pyran-2-yloxy)methyl)pyridin-2-yl)piperazine-1-carboxylate

HRID 517559Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 517559
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[CH:10]=1.Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>CO.[OH-].[Na+]>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([N:15]2[CH2:20][CH2:19][N:18]([C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])[CH2:17][CH2:16]2)[CH:10]=1

Komponenten

5

Edukt 2

HCID 10387Benzyl chloroformateHCID 867114981-(4-((tetrahydro-2H-pyran-2-yloxy)methyl)pyridin-2-yl)piperazine

Produkt 1

HCID 86711499benzyl 4-(4-((tetrahydro-2H-pyran-2-yloxy)methyl)pyridin-2-yl)piperazine-1-carboxylateAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

To a solution of 1-(4-((tetrahydro-2H-pyran-2-yloxy)methyl)pyridin-2-yl)piperazine (8.5 g, 30.6 mmol) in MeOH (30 mL), NaOH (2 M, 31 mL) was slowly added at RT, followed by the addition of benzyl chloroformate (6.4 g, 37 mmol) in portions at 0° C. The mixture was stirred at RT overnight. The solution was concentrated and diluted with H2O (500 mL), extracted with EtOAc (3×200 mL). The combined organic layers were washed with H2O (100 mL) and brine (50 mL), dried over Na2SO4, filtered, and concentrated to afford the crude product, which was purified by silica gel column chromatography (Petroleum ether:EtOAc=1:1) to afford benzyl 4-(4-((tetrahydro-2H-pyran-2-yloxy)methyl)pyridin-2-yl)piperazine-1-carboxylate as a yellow oil (7.3 g, 58%). MS (ES+) C23H29N3O4 requires: 411, found: 412[M+H]+.

Aufarbeitung

  1. concentrationThe solution was concentrated
  2. additiondiluted with H2O (500 mL)
  3. extractionextracted with EtOAc (3×200 mL)
  4. washThe combined organic layers were washed with H2O (100 mL) and brine (50 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford the crude product, which
  9. customwas purified by silica gel column chromatography (Petroleum ether:EtOAc=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-700a54ea03bc4284ade81f11679fbda5
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115120B2

Notizen zur Reaktion

Wird geladen…