Sodium Hydroxide → (8S)-octahydropyrrolo[1,2-a]pyrazin-8-ol

HRID 421213Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 421213
[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH:7][C@@H:8]1[CH:12]2[C:13](=O)[NH:14][CH2:15][C:16](=O)[N:11]2[CH2:10][CH2:9]1.[OH-].[Na+]>C1COCC1>[CH2:13]1[NH:14][CH2:15][CH2:16][N:11]2[CH2:10][CH2:9][C@H:8]([OH:7])[CH:12]12

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 59215828(8S)-8-hydroxyhexahydropyrrolo[1,2-a]pyrazine-1,4-dione

Produkt 1

HCID 55300579(8S)-octahydropyrrolo[1,2-a]pyrazin-8-olAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Into a stirred, cooled (0° C.) suspension of LiAlH4 (3.3 g, 88 mmol) in 60 ml of dry THF, was introduced (8S)-8-hydroxyhexahydropyrrolo[1,2-a]pyrazine-1,4-dione (D70, 750 mg, 4.4 mmol) in small portions. The mixture was then allowed to reach rt and stirred for 48 h, after which it was cooled to 0° C. THF was introduced (70 ml), then successively a saturated solution of Na—K-tartrate (5 ml) and a 20% aqueous NaOH solution (5 ml) were dropped into the flask, under vigorous stirring. The suspension was stirred for 30 min at rt, and filtered. The pale filter cake was washed with 100 ml of CHCl3 and the combined filtrates and washings were evaporated in vacuo to give 500 mg of the title compound. From GC-MS analysis 2 diastereomeric products were still observed. Yield 80%.

Aufarbeitung

  1. temperatureInto a stirred, cooled
  2. customto reach rt
  3. stirringThe suspension was stirred for 30 min at rt
  4. filtrationfiltered
  5. washThe pale filter cake was washed with 100 ml of CHCl3
  6. customthe combined filtrates and washings were evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e32205eb95a848f3ad81320f659390d1
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08097618B2

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