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Methanol → [2-Phenyl-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrol-3-yl]-methanol

HRID 1295355
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1295355
C([O:3][C:4]([C:6]12C[CH:10]1[CH2:9][N:8]([S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:7]2[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=O)C.C(OC(C1[C@H](C2C=CC=CC=2)N(S(C2C=CC(C)=CC=2)(=O)=O)CC=1)=O)C.CC(C[AlH]CC(C)C)C.CO>C(Cl)Cl>[C:22]1([CH:7]2[C:6]([CH2:4][OH:3])=[CH:10][CH2:9][N:8]2[S:12]([C:15]2[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=2)(=[O:14])=[O:13])[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 887MethanolHCID 14487Diisobutylaluminum hydrideHCID 589073302-Phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hexane-1-carboxylic acid ethyl esterHCID 69337074(S)-2-phenyl-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid ethyl ester

Produkt 1

HCID 58907347[2-Phenyl-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrol-3-yl]-methanol
Ausbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-25 °C

Versuchsvorschrift

To racemic intermediate 1, one enantiomer being (S)-2-phenyl-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid ethyl ester (1.8 g, 5.0 mmol), was dissolved in methylene chloride (60 mL) in a three necked flask equipped with an addition funnel and an internal thermometer. The mixture was cooled to −25° C., DIBAL (1M/toluene, 12.5 mL, 12.5 mmol) was added dropwise and the reaction stirred for an additional 0.5 hours. Methanol was added to the cold solution until gas evolution ceased and the solvents were then removed at reduced pressure. The residue was partitioned between a saturated solution of Rochelle's salt and methylene chloride. The organics were washed with brine, dried over sodium sulfate, filtered, and concentrated. The crude product was chromatographed on silica gel using a gradient of 20% to 60% ETOAc/Hexanes to yield the title compound as a sticky foam (1.6 g, 98% yield).

Aufarbeitung

  1. customequipped with an addition funnel
  2. customthe solvents were then removed at reduced pressure
  3. customThe residue was partitioned between a saturated solution of Rochelle's salt and methylene chloride
  4. washThe organics were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was chromatographed on silica gel using a gradient of 20% to 60% ETOAc/Hexanes

Quellen und Nachweise

ORD-Eintrag
ord-f781173d1846437ebbdbf294fb1807d2
Quelldatensatz
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07241798B2

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