Water → (S)-1,4-Dibenzyl-2-(3-methoxy-allyl)-piperazine

HRID 131408Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 131408
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Cl-].COC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:34]([N:41]1[CH2:46][CH2:45][N:44]([CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH2:43][C@@H:42]1CC=O)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.O.[CH2:58]1[CH2:62][O:61][CH2:60][CH2:59]1>>[CH2:34]([N:41]1[CH2:46][CH2:45][N:44]([CH2:47][C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)[CH2:43][C@@H:42]1[CH2:58][CH:59]=[CH:60][O:61][CH3:62])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Komponenten

6

Edukt 5

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 2733832Lithium HexamethyldisilazideHCID 59732114HCID 59732114, Verbindung

Produkt 1

HCID 69210439(S)-1,4-Dibenzyl-2-(3-methoxy-allyl)-piperazine

Versuchsvorschrift

Add LiHMDS (1M in THF, 21.38 mL, 21.38 mmol) to (methoxymethyl)triphenyl-phosphonium chloride (7.329 g, 21.38 mmol) in THF (51.0 mL) via syringe at 0° C. and stir. After 30 minutes, add (S)-(1,4-dibenzyl-piperazin-2-yl)-acetaldehyde (4.71 g, 15.27 mmol) in THF (51.0 mL) via syringe. Remove ice bath and stir at ambient temperature. After 4 hours, add water and extract with ethyl acetate twice. Combine the organic solution, dry over sodium sulfate, filter, and concentrate under reduced pressure to give crude residue. Purify the residue by flash chromatography, eluting with ethyl acetate:hexane (40:60) to give the title compound: mass spectrum (m/e):337.18 (M+1).

Aufarbeitung

  1. stirringRemove ice bath and stir at ambient temperature
  2. waitAfter 4 hours
  3. extractionextract with ethyl acetate twice
  4. dry with materialdry over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure
  7. customto give crude residue
  8. customPurify the residue by flash chromatography
  9. washeluting with ethyl acetate:hexane (40:60)

Quellen und Nachweise

ORD-Eintrag
ord-1a749b0c2b2f46a8ae6ffce0b49ce1a2
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384934B2

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