2,4-Difluoronitrobenzene → (S)-tert-butyl 3-(5-fluoro-2-nitrophenoxy)piperidine-1-carboxylate

HRID 240593Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 240593
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[C:11]([N:18]1[CH2:23][CH2:22][CH2:21][C@H:20]([OH:24])[CH2:19]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].F[C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=1[N+:33]([O-:35])=[O:34]>C1COCC1>[F:32][C:30]1[CH:29]=[CH:28][C:27]([N+:33]([O-:35])=[O:34])=[C:26]([CH:31]=1)[O:24][C@H:20]1[CH2:21][CH2:22][CH2:23][N:18]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:19]1

Komponenten

5

Edukt 3

HCID 679672,4-DifluoronitrobenzeneHCID 1514399tert-butyl (3S)-3-hydroxypiperidine-1-carboxylateHCID 2733832Lithium Hexamethyldisilazide

Produkt 1

HCID 58413048(S)-tert-butyl 3-(5-fluoro-2-nitrophenoxy)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

LiHMDS 1M solution in THF (6.4 ml) was added into a solution of (S)-1-Boc-3-hydroxypiperidine (1.3 g) in anhydrous THF (20.0 ml). The reaction was stirred at 0° C. for 0.5 h. Then 2,4-difluoro-1-nitro-benzene (703 μl) was added in a single portion. The reaction was allowed to warm to room temperature overnight when TLC indicated the consumption of the starting material. The reaction was quenched by addition of sat NH4Cl (5.0 ml) and diluted with EtOAc (100.0 ml). The organic layer was washed with sat. NH4Cl (50.0 ml) and the aqueous back extracted with EtOAc. The combined organic phases were washed with brine, dried, filtered and concentrated in vacuo. The residue was purified by chromatography to give the intended product.

Aufarbeitung

  1. temperatureto warm to room temperature overnight when TLC
  2. customthe consumption of the starting material
  3. customThe reaction was quenched by addition of sat NH4Cl (5.0 ml)
  4. additiondiluted with EtOAc (100.0 ml)
  5. washThe organic layer was washed with sat. NH4Cl (50.0 ml)
  6. extractionthe aqueous back extracted with EtOAc
  7. washThe combined organic phases were washed with brine
  8. customdried
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by chromatography
  12. customto give the intended product

Quellen und Nachweise

ORD-Eintrag
ord-c87fc213343f4e9686a2ea816111b1b2
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648068B2

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