1,2-Diaminocyclohexane, trans- → (S)-tert-butyl 4-(3-(6-(methylsulfonyl)pyridin-3-yloxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate

HRID 407947Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 407947
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:18][CH2:17][C@H:16]([O:19][C:20]3[CH:21]=[N:22][C:23](Br)=[CH:24][CH:25]=3)[C:15]2=[O:27])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:28]([S:30]([O-:32])=[O:31])C.[Na+].[C@@H]1(N)CCCC[C@H]1N>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:18][CH2:17][C@H:16]([O:19][C:20]3[CH:21]=[N:22][C:23]([S:30]([CH3:28])(=[O:32])=[O:31])=[CH:24][CH:25]=3)[C:15]2=[O:27])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 438061,2-Diaminocyclohexane, trans-HCID 22986214Sodium EthanesulfinateHCID 86688100(S)-tert-butyl-4-(3-(6-bromopyridin-3-yloxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate

Produkt 1

HCID 66800509(S)-tert-butyl 4-(3-(6-(methylsulfonyl)pyridin-3-yloxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylateAusbeute 100,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A solution of (S)-tert-butyl-4-(3-(6-bromopyridin-3-yloxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate (315 mg, 0.714 mmol) in degassed DMSO (5 mL) was added sodium ethanesulfinate (117 mg, 1.15 mmol), trans-cyclohexane-1,2-diamine (33 mg, 0.286 mmol) and Cu(I) triflate benzene complex (54 mg, 0.107 mmol). The reaction was heated to 110° C. for 12 hours at which point the reaction was cooled to ambient temperature and partitioned between water (5 mL) and EtOAc (10 mL). The organic layer was separated and the aqueous layer extracted with EtOAc (2×5 mL). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. The resulting material was purified by silica gel chromatography eluting with 1:1 hexanes/EtOAc to yield (S)-tert-butyl-4-(3-(6-(methylsulfonyl)pyridine-3-yloxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate (315 mg, 94%) as a white solid.

Aufarbeitung

  1. temperaturewas cooled to ambient temperature
  2. custompartitioned between water (5 mL) and EtOAc (10 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted with EtOAc (2×5 mL)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting material was purified by silica gel chromatography
  9. washeluting with 1:1 hexanes/EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-f454c60ea7bc4b48aeb6febbd74047c9
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754226B2

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