Ammonium → tert-butyl (3S)-1-(1-(6-fluoropyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate

HRID 339074Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 339074
[NH:1]1[CH2:5][CH2:4][C@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:2]1.[F:14][C:15]1[N:20]=[CH:19][C:18]([C:21](=O)[CH3:22])=[CH:17][CH:16]=1.[BH4-].[Na+].[NH4+]>C1COCC1.C(O[Ti](OC(C)C)(OC(C)C)OC(C)C)(C)C.C(OCC)(=O)C.O.C(O)C>[F:14][C:15]1[N:20]=[CH:19][C:18]([CH:21]([N:1]2[CH2:5][CH2:4][C@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])[CH2:2]2)[CH3:22])=[CH:17][CH:16]=1

Komponenten

10

Edukt 4

HCID 223AmmoniumHCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 4311764Sodium borohydrideHCID 130903391-(6-Fluoropyridin-3-yl)ethan-1-one

Produkt 1

HCID 86707550tert-butyl (3S)-1-(1-(6-fluoropyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamateAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 178460666HCID 178460666, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (S)-tert-butyl pyrrolidin-3-ylcarbamate (0.94 g, 5.04 mmol), 1-(6-fluoropyridin-3-yl)ethanone (0.35 g, 2.52 mmol) in THF (10 mL) was added tetraisopropoxytitanium (1.48 mL, 5.04 mmol) and the reaction mixture was stirred at ambient temperature for 18 hours. Ethanol (2 mL) and NaBH4 (0.38 g, 10.1 mmol) were added and the mixture was stirred at ambient temperature for 2 hours. Water (10 mL), concentrated ammonium (2 mL) and ethyl acetate (20 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue obtained was purified by flash chromatography on silica gel (1:1 hexane/ethyl acetate) to give tert-butyl (3S)-1-(1-(6-fluoropyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate (0.343 g, 44.0%) as solid.

Aufarbeitung

  1. stirringthe mixture was stirred at ambient temperature for 2 hours
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. customwas purified by flash chromatography on silica gel (1:1 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-2e451b7205104ef7aa048b8265d4bd09
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889704B2

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