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Aluminium lithium hydride → 1,1-Dimethylethyl (2S,4S)-2-formyl-4-methyl-1-pyrrolidinecarboxylate

HRID 2172502
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2172502
CON(C)[C:4]([C@@H:6]1[CH2:10][C@H:9]([CH3:11])[CH2:8][N:7]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH:4]([C@@H:6]1[CH2:10][C@H:9]([CH3:11])[CH2:8][N:7]1[C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])=[O:5]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 58580932HCID 58580932, Verbindung

Produkt 1

HCID 538677451,1-Dimethylethyl (2S,4S)-2-formyl-4-methyl-1-pyrrolidinecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

(2S,4S)-tert-butyl 2-(methoxy(methyl)carbamoyl)-4-methylpyrrolidine-1-carboxylate (5.30 g, 19.5 mmol) was dissolved in 120 mL THF, cooled to −78° C. and treated with lithium aluminum hydride (1M in THF, 19.5 mL, 19.5 mmol) dropwise via addition funnel. After 1 hour, the mixture was brought to 0° C. and kept at that temperature for 2 hours. It was quenched by dropwise addition of a 50 mL solution of 3.0 g KHSO4 in water, removed from the ice bath, and stirred 15 minutes at room temperature. The product was extracted with three 75 mL portions of ethyl acetate and washed with brine. The organic phase was dried over sodium sulphate, filtered, and concentrated to give crude (2S,4S)-tert-butyl 2-formyl-4-methylpyrrolidine-1-carboxylate. (4.89 g)

Aufarbeitung

  1. customwas brought to 0° C.
  2. waitkept at that temperature for 2 hours
  3. customIt was quenched by dropwise addition of a 50 mL solution of 3.0 g KHSO4 in water
  4. customremoved from the ice bath
  5. extractionThe product was extracted with three 75 mL portions of ethyl acetate
  6. washwashed with brine
  7. dry with materialThe organic phase was dried over sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-02f20f82d740413d8def72e3563b2c30
Quelldatensatz
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09051340B2

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