Sodium Fluoride → tert-butyl(2S)-2-(azetidin-1-ylcarbonyl)-4-fluoropyrrolidine-1-carboxylate

HRID 490136

Reaktionsgleichung

Reaktionsgleichung von HRID 490136
[F:1]C(F)(N(CC)CC)C(F)C(F)(F)F.[N:15]1([C:19]([C@@H:21]2[CH2:25][C@H:24](O)[CH2:23][N:22]2[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:20])[CH2:18][CH2:17][CH2:16]1.[F-].[Na+].C(=O)([O-])[O-].[K+].[K+]>ClCCl.C(OCC)(=O)C>[N:15]1([C:19]([C@@H:21]2[CH2:25][CH:24]([F:1])[CH2:23][N:22]2[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:20])[CH2:18][CH2:17][CH2:16]1

Komponenten

7

Edukt 4

HCID 5235Sodium FluorideHCID 11430Potassium CarbonateHCID 136149N,N-Diethyl-1,1,2,3,3,3-hexafluoropropylamineHCID 67429167tert-butyl(2S,4S)-2-(azetidin-1-ylcarbonyl)-4-hydroxypyrrolidine-1-carboxylate

Produkt 1

HCID 67429147tert-butyl(2S)-2-(azetidin-1-ylcarbonyl)-4-fluoropyrrolidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2.68 g of a mixture (approximately 3:1) of 1,1,2,3,3,3-hexafluoro-1-(diethylamino)propane and 1,2,3,3,3-pentafluoro-1-(diethylamino)-2-propene was added dropwise over a period of 10 minutes under ice cooling to a suspension of 2.71 g of the compound obtained in step 7-1 and 505 mg of sodium fluoride in 27 mL of dichloromethane, after which the reaction mixture was stirred for 16 hours at room temperature. 100 mL of a 5% potassium carbonate aqueous solution was added under ice cooling to the reaction solution, and the reaction mixture was stirred for 30 minutes at the same temperature. After liquid separation, the aqueous layer thus obtained was extracted with chloroform (30 mL×2), and the combined organic layer was washed with 50 mL of saturated brine and dried with magnesium sulfate, after which the drying agent was filtered off and the solvent was distilled off under reduced pressure. The residue thus obtained was subjected to column chromatography (silica gel 60, mobile phase: ethyl acetate) to obtain 2.30 g of the titled compound (colorless oil).

Aufarbeitung

  1. stirringthe reaction mixture was stirred for 30 minutes at the same temperature
  2. customAfter liquid separation
  3. customthe aqueous layer thus obtained
  4. extractionwas extracted with chloroform (30 mL×2)
  5. washthe combined organic layer was washed with 50 mL of saturated brine
  6. dry with materialdried with magnesium sulfate
  7. filtrationafter which the drying agent was filtered off
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue thus obtained

Quellen und Nachweise

ORD-Eintrag
ord-6f9469ed3f7f4ba4be928fc143428627
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528124B2

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