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1-Pyrrolidinecarboxylic acid, 2-oxo-, 1,1-dimethylethyl ester → tert-butyl N-[4-(3-fluorophenyl)-4-oxobutyl]carbamate

HRID 63992
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 63992
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[F:14][C:15]1[CH:16]=[C:17]([Mg]Br)[CH:18]=[CH:19][CH:20]=1>C1COCC1>[F:14][C:15]1[CH:20]=[C:19]([C:2](=[O:1])[CH2:6][CH2:5][CH2:4][NH:3][C:7](=[O:8])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH:18]=[CH:17][CH:16]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 3790001-Pyrrolidinecarboxylic acid, 2-oxo-, 1,1-dimethylethyl esterHCID 178505773HCID 178505773, Verbindung

Produkt 1

HCID 67330612tert-butyl N-[4-(3-fluorophenyl)-4-oxobutyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

In a round-bottomed flask was charged tert-butyl 2-oxopyrrolidine-1-carboxylate (2.2 g, 11.9 mmol) and THF (25 mL). The mixture was cooled down to −78° C. first, followed by slow addition of (3-fluorophenyl)magnesium bromide (17.8 mL, 17.8 mmol, 1.0 M solution in THF) over 15 minutes. The mixture was stirred for 3 hours, during which time the bath temperature rose from −78° C. to −10° C. The reaction was quenched by drop-wise addition of 1N HCl (2 mL) and warmed up to ambient temperature, followed by addition of EtOAc and water. After separating the organic layer, the aqueous layer was extracted with EtOAc three times. The combined organic layers was dried over Na2SO4 and concentrated to yield the product as a clear oil.

Aufarbeitung

  1. customrose from −78° C. to −10° C
  2. customThe reaction was quenched by drop-wise addition of 1N HCl (2 mL)
  3. temperaturewarmed up to ambient temperature
  4. additionfollowed by addition of EtOAc and water
  5. customAfter separating the organic layer
  6. extractionthe aqueous layer was extracted with EtOAc three times
  7. dry with materialThe combined organic layers was dried over Na2SO4
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0e0d6802bbec4410b6ba92c729e66ce8
Quelldatensatz
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09447104B2

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