Aluminium lithium hydride → (γS)-4-(Methylsulfonyl)-γ-phenylbenzenepropanol

HRID 1593015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1593015
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C@H:11]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:12][C:13](N2[C@H](C3C=CC=CC=3)[C@H](C)N(C)C2=O)=[O:14])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[C:29]1([C@@H:11]([C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:10][CH:9]=2)[CH2:12][CH2:13][OH:14])[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 69264112HCID 69264112, Verbindung

Produkt 1

HCID 69264553(γS)-4-(Methylsulfonyl)-γ-phenylbenzenepropanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (4S,5R)-1-[(S)-3-(4-methanesulfonyl-phenyl)-3-phenyl-propionyl]-3,4-dimethyl-5-phenyl-imidazolidin-2-one (846 mg, 1.78 mmol) in THF (20 mL) at 0° C. was added lithium aluminium hydride (3.6 mL, 1M in THF, 3.6 mmol) and the resulting mixture was stirred for 15 min. The reaction was quenched by the addition of 2M aqueous sodium hydroxide. The phases were separated and the organic phase pre-absorbed onto a Bond Elut and eluted with a gradient of isohexane to ethyl acetate giving the sub-titled compound as a white solid (285 mg, 55%); NMR (CDCl3): 1.63 (br s, 1H), 2.33 (m, 2H), 3.00 (s, 3H), 3.59 (t, 2H), 4.28 (t, 1H), 7.23 (m, 5H), 7.43 (d, 2H), 7.82 (d, 2H).

Aufarbeitung

  1. customThe reaction was quenched by the addition of 2M aqueous sodium hydroxide
  2. customThe phases were separated
  3. customthe organic phase pre-absorbed onto a Bond Elut
  4. washeluted with a gradient of isohexane to ethyl acetate giving the sub-titled compound as a white solid (285 mg, 55%)

Quellen und Nachweise

ORD-Eintrag
ord-d5db36baf44d4d229ce0efdac31727f6
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07294636B2

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