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Methyl (2S)-1-methyl-5-oxoprolinate → (5S)-5-(Hydroxymethyl)-1-methyl-2-pyrrolidinone

HRID 59714
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 59714
[CH3:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C@H:3]1[C:8](OC)=[O:9].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:9][CH2:8][C@H:3]1[N:2]([CH3:1])[C:6](=[O:7])[CH2:5][CH2:4]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 12361160Methyl (2S)-1-methyl-5-oxoprolinateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 14876039(5S)-5-(Hydroxymethyl)-1-methyl-2-pyrrolidinoneAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A stirred solution of 0.68 g (4.33 mmole) (S)-Methyl 1-methyl-5-oxopyrrolidine-2-carboxylate in 15 ml dry tetrahydrofuran was cooled to −78° C. and under argon atmosphere, 2.2 ml (2.2 mmole) of 1M lithium aluminum hydride solution in tetrahydrofuran was added drop by drop during 20 minutes, stirred at −78° C. for 1 hour and removing the cooling bath left to warm up to 0° C. at stirring. While ice cooling, 0.22 ml 10% of sodium hydroxide aqueous solution was added, stirred for 10 minutes, then 0.22 ml of water was added and the reaction mixture stirred for 1.5 hours allowing it to warm to room temperature. The precipitate was filtered and washed with 5×2 ml of ethyl acetate. The combined filtrates were dried over magnesium sulfate and evaporated at 35° C. in good vacuum, giving 0.52 g (93%) product which was pure enough for the next step.

Aufarbeitung

  1. customremoving the cooling bath
  2. waitleft
  3. temperatureto warm up to 0° C.
  4. stirringat stirring
  5. additionWhile ice cooling, 0.22 ml 10% of sodium hydroxide aqueous solution was added
  6. stirringstirred for 10 minutes
  7. addition0.22 ml of water was added
  8. stirringthe reaction mixture stirred for 1.5 hours
  9. temperatureto warm to room temperature
  10. filtrationThe precipitate was filtered
  11. washwashed with 5×2 ml of ethyl acetate
  12. dry with materialThe combined filtrates were dried over magnesium sulfate
  13. customevaporated at 35° C. in good vacuum

Quellen und Nachweise

ORD-Eintrag
ord-a66d95f33d144bf4ba017109b5d87857
Quelldatensatz
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09440948B2

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