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Ammonium Chloride → (NE,S)-N-[(3aR,6aS)-2-benzyl-1,3,3a,5,6,6a-hexahydrocyclopenta[c]pyrrol-4-ylidene]-2-methylpropane-2-sulfinamide

HRID 1092469
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1092469
[CH2:1]([N:8]1[CH2:12][CH:11]2[C:13](=O)[CH2:14][CH2:15][CH:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][C:18]([S@@:21]([NH2:23])=[O:22])([CH3:20])[CH3:19].[Cl-].[NH4+]>O1CCCC1.[O-]CC.[O-]CC.[O-]CC.[O-]CC.[Ti+4]>[CH2:1]([N:8]1[CH2:12][C@@H:11]2/[C:13](=[N:23]/[S@:21]([C:18]([CH3:20])([CH3:19])[CH3:17])=[O:22])/[CH2:14][CH2:15][C@@H:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:1]([N:8]1[CH2:12][C@H:11]2/[C:13](=[N:23]/[S@:21]([C:18]([CH3:20])([CH3:19])[CH3:17])=[O:22])/[CH2:14][CH2:15][C@H:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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Komponenten

7

Edukt 3

HCID 25517Ammonium ChlorideHCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 134637692-Benzylhexahydrocyclopenta[c]pyrrol-4(1H)-one

Produkt 2

HCID 87063925(NE,S)-N-[(3aR,6aS)-2-benzyl-1,3,3a,5,6,6a-hexahydrocyclopenta[c]pyrrol-4-ylidene]-2-methylpropane-2-sulfinamideHCID 87063931
(NE,S)-N-[(3aS,6aR)-2-benzyl-1,3,3a,5,6,6a-hexahydrocyclopenta[c]pyrrol-4-ylidene]-2-methylpropane-2-sulfinamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 76524Titanium tetraethoxideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

2-Benzylhexahydrocyclopenta[c]pyrrol-4(5H)-one (16.28 g, 76 mmol), titanium tetraethoxide (28.5 mL, 137 mmol), and (S)-2-methylpropane-2-sulfinamide (10.452 g, 86 mmol) were combined in tetrahydrofuran (200 mL). The reaction was heated at 60° C. overnight. The reaction was then reduced in volume to about half and poured into 150 mL of saturated aqueous ammonium chloride. The precipitate was collected by filtration and washed with ethyl acetate. The filtrate was poured into a separatory funnel and the organic layer was removed. The aqueous layer was extracted with ethyl acetate (3×100 mL). The organic washes were combined and washed with brine, dried (Na2SO4) and concentrated. The crude material was chromatographed using silica gel cartridge (Analogix®, Burlington, Wis., RS65-400) eluting with 5-100% ethyl acetate/hexanes to give (S,E)-N-((3aR,6aS)-2-benzylhexahydrocyclopenta[c]pyrrol-4(5H)-ylidene)-2-methylpropane-2-sulfinamide and (S,E)-N-((3aS,6aR)-2-benzylhexahydrocyclopenta[c]pyrrol-4(5H)-ylidene)-2-methylpropane-2-sulfinamide.

Aufarbeitung

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with ethyl acetate
  3. additionThe filtrate was poured into a separatory funnel
  4. customthe organic layer was removed
  5. extractionThe aqueous layer was extracted with ethyl acetate (3×100 mL)
  6. washwashed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe crude material was chromatographed
  10. washeluting with 5-100% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-7841094fb00340aaa056177672875079
Quelldatensatz
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08129417B2

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