Lithium aluminum hydride → (2S,4R)-4-Phenyl-2-pyrrolidinemethanol

HRID 969187Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 969187
[AlH4-].[Li+].[C:3]1([C@@H:9]2[CH2:13][NH:12][C@H:11]([C:14](OC)=[O:15])[CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>O1CCCC1>[C:3]1([C@@H:9]2[CH2:13][NH:12][C@H:11]([CH2:14][OH:15])[CH2:10]2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Komponenten

4

Edukt 2

HCID 28112Lithium aluminum hydrideHCID 14102971HCID 14102971, Verbindung

Produkt 1

HCID 57368261(2S,4R)-4-Phenyl-2-pyrrolidinemethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Lithium tetrahydroaluminate in tetrahydrofuran (1.00 M, 1.00 mL) was added to methyl (2S,4R)-4-phenylpyrrolidine-2-carboxylate (103.0 mg, 0.0005018 mol) in tetrahydrofuran (3.00 mL, 0.0370 mol) at 0° C. Then the ice-water bath was removed and the reaction mixture was stirred at rt for 1 h and was quenched with brine (1 mL). The resulting mixture was extracted with ethyl acetate (2×2 mL). The combined organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give the desired product which was directly used in the next step without further purification.

Aufarbeitung

  1. customThen the ice-water bath was removed
  2. customwas quenched with brine (1 mL)
  3. extractionThe resulting mixture was extracted with ethyl acetate (2×2 mL)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d8838ed23063426a978ec7878b4360ea
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07304081B2

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