N-bromobutanimide → Tert-butyl 4-(3-bromo-2-oxopropyl)piperidine-1-carboxylate

HRID 335259Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 335259
C[Si](C)(C)[O:3][C:4](=[CH2:19])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.C(=O)(O)[O-].[Na+].[Br:27]N1C(=O)CCC1=O>C1COCC1>[Br:27][CH2:3][C:4](=[O:19])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1

Komponenten

5

Edukt 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 66994845Tert-butyl 4-(2-(trimethylsilyloxy)allyl)piperidine-1-carboxylate

Produkt 1

HCID 22243583Tert-butyl 4-(3-bromo-2-oxopropyl)piperidine-1-carboxylateAusbeute 110 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 4-(2-(trimethylsilyloxy)allyl)piperidine-1-carboxylate (6.43 g, 20.5 mmol) in THF (100 mL) at 0° C. was added sodium bicarbonate (2.58 g, 30.7 mmol) followed by 1-bromopyrrolidine-2,5-dione (3.65 g, 20.5 mmol). Warmed to ambient temperature and stirred 90 minutes. Partitioned between ether (150 mL) and saturated sodium bicarbonate. The aqueous layer was reextracted with ether (100 mL). The combined organic layers were washed with saturated bicarbonate, brine, dried, and concentrated to afford the title compound (7.2 g, 110% yield) as a yellow oil. Purity was 85% with the major impurity being succinimide. The crude material was used in the next step.

Aufarbeitung

  1. customPartitioned between ether (150 mL) and saturated sodium bicarbonate
  2. washThe combined organic layers were washed with saturated bicarbonate, brine
  3. customdried
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b6a96567cc93453095c43d430fa080d7
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883828B2

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