Sodium hydride → Ethyl 5-[8-(t-Butoxycarbonyl)-4-keto-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl]pentanoate

HRID 975782Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 975782
[C:1]([O:5][C:6]([N:8]1[CH2:24][CH2:23][C:11]2([N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:14][NH:13][C:12]2=[O:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]2([N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:14][N:13]([CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:12]2=[O:22])[CH2:23][CH2:24]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 84580Ethyl 5-bromovalerateHCID 389488tert-Butyl 4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate

Produkt 1

HCID 67722997Ethyl 5-[8-(t-Butoxycarbonyl)-4-keto-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl]pentanoateAusbeute 75,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of 2.3 g (6.95 mmol) of 8-(t-butoxycarbonyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one in 40 ml of dry dimethylformamide at 0° C. was added 0.4 g (13 mmol) of sodium hydride (80% in mineral oil). The mixture was stirred at 0° C. under argon for 30 minutes and then ethyl 5-bromopentanoate (2.09 g, 10 mmol) was added dropwise. After being allowed to come to ambient temperature, the mixture was stirred for an additional 20 hours. The mixture was quenched with aqueous ammonium chloride, diluted with water and extracted with ethyl acetate. The extracts were washed with water, dried over magnesium surf ate and concentrated. The residue was purified by column chromatography (silica gel, 0-25% gradient of ethyl acetate in hexane) to provide 2.4 g (75.2%) of the indicated ester as a colorless liquid.

Aufarbeitung

  1. customto come to ambient temperature
  2. stirringthe mixture was stirred for an additional 20 hours
  3. customThe mixture was quenched with aqueous ammonium chloride
  4. additiondiluted with water
  5. extractionextracted with ethyl acetate
  6. washThe extracts were washed with water
  7. dry with materialdried over magnesium
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography (silica gel, 0-25% gradient of ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-c9c4d599922640048035aecf5d9924c5
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05610142

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