1,4-Dioxane → Tert-butyl 4-{[6-formyl-2-(trifluoromethyl)pyrimidin-4-yl]amino}piperidine-1-carboxylate

HRID 717883Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 717883
C(O/C=C\[C:6]1[N:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[N:9]=[C:8]([NH:16][CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]2)[CH:7]=1)C.I([O-])(=O)(=O)=O.[Na+].[O:36]1CCOC[CH2:37]1>O.[Os](=O)(=O)(=O)=O>[CH:37]([C:6]1[N:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[N:9]=[C:8]([NH:16][CH:17]2[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][CH2:22]2)[CH:7]=1)=[O:36]

Komponenten

6

Edukt 3

HCID 312751,4-DioxaneHCID 23667635Sodium periodateHCID 86706862tert-butyl 4-{[6-[(Z)-2-ethoxyvinyl]-2-(trifluoromethyl)pyrimidin-4-yl]amino}piperidine-1-carboxylate

Produkt 1

HCID 86706863Tert-butyl 4-{[6-formyl-2-(trifluoromethyl)pyrimidin-4-yl]amino}piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318Osmium TetroxideKatalysatorHCID 962WaterLösungsmittel2×

Versuchsvorschrift

tert-Butyl 4-{[6-[(Z)-2-ethoxyvinyl]-2-(trifluoromethyl)pyrimidin-4-yl]amino}piperidine-1-carboxylate (0.80 g, 1.9 mmol, from Step 2) was dissolved in 1,4-dioxane (56 mL) and water (14 mL), then sodium periodate (1.2 g, 5.8 mmol) was added followed by osmium tetraoxide (4 wt % in water, 0.424 mL, 0.0666 mmol). After stirring for 24 hours, the reaction mixture was partitioned between water and EtOAc, the phases were separated and the aqueous phase was extracted with additional EtOAc. The combined organic extracts were washed with water, then sat'd NaCl, dried over Na2SO4, filtered and solvent removed in vacuo. The crude product was used in the next reaction without purification. LCMS (M+H)+: 375.0; (M+H2O+H)+: 393.0.

Aufarbeitung

  1. customthe reaction mixture was partitioned between water and EtOAc
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted with additional EtOAc
  4. washThe combined organic extracts were washed with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customsolvent removed in vacuo
  8. customThe crude product was used in the next reaction without purification

Quellen und Nachweise

ORD-Eintrag
ord-10d56eae0c6e44028d0e2ce66a2effa0
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193733B2

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