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Acetone → [1,1-Dioxo-(3R,4S)-4-[(R)-1-phenyl-ethylamino]-tetrahydrothiophen-3-yl]-[(S)-3-(4-fluoro-benzyl)-piperidin-1-yl]-methanone

HRID 497498
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 497498
[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C@@H:7]2[CH2:12][CH2:11][CH2:10][N:9]([C:13]([C@H:15]3[C@H:19]([NH:20][C@@H:21]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH3:22])[CH2:18]S[CH2:16]3)=[O:14])[CH2:8]2)=[CH:4][CH:3]=1.CC(C)=O.O.[S:36]([O-:41])(O[O-])(=O)=[O:37].[K+].[K+]>CO>[O:37]=[S:36]1(=[O:41])[CH2:18][C@@H:19]([NH:20][C@@H:21]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH3:22])[C@H:15]([C:13]([N:9]2[CH2:10][CH2:11][CH2:12][C@@H:7]([CH2:6][C:5]3[CH:29]=[CH:30][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:8]2)=[O:14])[CH2:16]1
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Komponenten

6

Edukt 4

HCID 180AcetoneHCID 962WaterHCID 10313463Potassium peroxymonosulphateHCID 69747757[(S)-3-(4-fluorobenzyl)-piperidin-1-yl]-[(3R,4S)-4-((R)-1-phenyl-ethylamino)-tetrahydrothiophen-3-yl]-methanone

Produkt 1

HCID 69747758[1,1-Dioxo-(3R,4S)-4-[(R)-1-phenyl-ethylamino]-tetrahydrothiophen-3-yl]-[(S)-3-(4-fluoro-benzyl)-piperidin-1-yl]-methanone
Ausbeute 72,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

[(S)-3-(4-fluorobenzyl)-piperidin-1-yl]-[(3R,4S)-4-[(R)-1-phenyl-ethylamino]-tetrahydro-thiophen-3-yl]-methanone (1.02 g, 2.39 mmol) was dissolved in methanol (10 mL) and acetone (10 mL) and stirred on ice. Water (10 mL) was added, and the resulting heterogeneous mixture was treated with potassium peroxymonosulfate (Oxone®, 3.67 g, 5.98 mmol). After 5 min the cooling bath was removed and the mixture was stirred at room temperature. After 20.5 h, the mixture was concentrated and diluted with water. The pH was adjusted to ca. 11 with 1N sodium hydroxide, and the mixture was extracted with ethyl acetate. The combined extracts were dried (Na2SO4) and concentrated, and the residue was purified by flash column chromatography (2.5% 2-propanol/chloroform) to provide the product as a glass (790 mg, 72%).

Aufarbeitung

  1. customAfter 5 min the cooling bath was removed
  2. concentrationthe mixture was concentrated
  3. additiondiluted with water
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe combined extracts were dried (Na2SO4)
  6. concentrationconcentrated
  7. customthe residue was purified by flash column chromatography (2.5% 2-propanol/chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-4d46823343eb4b50a5f4d8724a493774
Quelldatensatz
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06949546B2

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