Water → ((S)-1-((S)-1-phenylethyl)pyrrolidin-3-yl)methanol

HRID 2382984Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2382984
[H-].[H-].[H-].[H-].[Li+].[Al+3].O=[C:8]1[N:12]([C@H:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:14])[CH2:11][C@@H:10]([C:21](OC)=[O:22])[CH2:9]1.O.[OH-].[Na+]>C1COCC1>[C:15]1([C@@H:13]([N:12]2[CH2:8][CH2:9][C@H:10]([CH2:21][OH:22])[CH2:11]2)[CH3:14])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 13772856HCID 13772856, VerbindungHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 11084986((S)-1-((S)-1-phenylethyl)pyrrolidin-3-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of LAH (20 g, 0.526 mol) in dried THF (400 mL) was added dropwise a solution of (S)-methyl 5-oxo-1-((S)-1-phenylethyl)pyrrolidine-3-carboxylate (M4) (50 g, 0.202 mol) in dried THF (50 mL) at 0° C. The mixture was heated to reflux overnight. The reaction mixture was cooled to 0° C. and treated with water (20 mL) and aqueous NaOH (10%, 20 mL). The slurry formed was filtered off and washed with THF. The combined filtrate was evaporated to give compound ((S)-1-((S)-1-phenylethyl)pyrrolidin-3-yl)methanol (M5), which was used directly in the next step.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customThe slurry formed
  4. filtrationwas filtered off
  5. washwashed with THF
  6. customThe combined filtrate was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-9ccd7b7f9e7645a1abf4a19b682b2320
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263605B2

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