Sodium hydride → Ethyl 5-methoxy-1-oxo-1,3-dihydrospiro[indene-2,4'-piperidine]-1'-carboxylate

HRID 713403Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 713403
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6]2.[CH2:13]([O:15][C:16](=[O:24])[N:17]([CH2:21][CH2:22]Br)[CH2:18][CH2:19]Br)[CH3:14].[H-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[C:7]1([CH2:22][CH2:21][N:17]([C:16]([O:15][CH2:13][CH3:14])=[O:24])[CH2:18][CH2:19]1)[CH2:6]2

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 787875-Methoxyindan-1-oneHCID 10924683Ethyl bis(2-bromoethyl)carbamate

Produkt 1

HCID 71227303Ethyl 5-methoxy-1-oxo-1,3-dihydrospiro[indene-2,4'-piperidine]-1'-carboxylateAusbeute 31,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a stirred solution of 5-methoxy-1-indanone (1.0 g, 6.17 mmol) and bis-(2-bromo-ethyl)-carbamic acid ethyl ester (1.87 g, 6.17) in DMF (10 mL) at 50° C. was added NaH (0.370 g, 15.4 mmol) by small portions. After being stirred at 50° C. for 16 hr, the reaction was cooled to ambient temperature. The reaction was diluted with 15 mL of ethyl acetate and washed twice with 10 mL of water, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash column (gradient of 85:15 to 60:40 heptane/ethyl acetate over 30 min) to give the title compound (590 mg, 1.945 mmol). MS calculated for C17H22NO4 304.4. found (ESI) m/z 304.2 (M+H)+, retention time 1.56 min.

Aufarbeitung

  1. temperaturethe reaction was cooled to ambient temperature
  2. washwashed twice with 10 mL of water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash column (gradient of 85:15 to 60:40 heptane/ethyl acetate over 30 min)

Quellen und Nachweise

ORD-Eintrag
ord-43c8330ffbaa4b3ab83710c9a5301053
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181266B2

Notizen zur Reaktion

Wird geladen…