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Tetrahydrofuran → HCID 12638305, Verbindung

HRID 1980037
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1980037
[O:1]=[C:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:3]1[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:18][CH:17]=1.C1COCC1.[H-].[Na+].Br[CH2:38][C:39]([O:41][CH3:42])=[O:40]>O>[C:11]([O:10][C:8]([N:4]1[CH2:5][CH2:6][N:7]([CH2:38][C:39]([O:41][CH3:42])=[O:40])[C:2](=[O:1])[CH:3]1[CH2:15][C:16]1[CH:17]=[CH:18][C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:20][CH:21]=1)=[O:9])([CH3:13])([CH3:14])[CH3:12]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 12638302HCID 12638302, Verbindung

Produkt 1

HCID 12638305HCID 12638305, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962Water
Lösungsmittel

Versuchsvorschrift

To a solution of t-boc-(4-benzyloxybenzyl)piperazinone 3a (2.66 g, 6.72×10-3 mole) and dry THF (20 ml) under argon at room temperature is added portionwise NaH (0.30 g, 7.4×10-3 mole, 59% oil dispersion). After stirring 1/2 hour at room temperature a solution of methyl α-bromoacetate (0.62 ml, 7.4×10-3 mole) is added via syringe. After stirring overnight the reaction mixture is poured into water which is subsequently extracted with Et2O (3 times). The combined ethereal extracts are washed with saturated aqueous NaCl before being dried over Na2SO4. Filtration of the drying agent and evaporation of the filtrate affords a viscous oil which after column chromatography (silica gel, 10% EtOAc/CHCl3) gives a clear, colorless oil. After standing in the refrigerator this oil crystallizes. The resulting solid is triturated with hexane and collected by filtration affording 4a as colorless matted needles: 2.3 g (74%), m.p. 84°-87° C.

Aufarbeitung

  1. additionis added via syringe
  2. extractionis subsequently extracted with Et2O (3 times)
  3. washThe combined ethereal extracts are washed with saturated aqueous NaCl
  4. dry with materialbefore being dried over Na2SO4
  5. filtrationFiltration of the drying agent and evaporation of the filtrate
  6. customaffords a viscous oil which after column chromatography (silica gel, 10% EtOAc/CHCl3)
  7. customgives a clear, colorless oil
  8. customcrystallizes
  9. customThe resulting solid is triturated with hexane
  10. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-bb699466b32e4b53a8d428886cf96354
Quelldatensatz
uspto-grants-1984_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04483988

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