N-bromobutanimide → Tert-butyl 8-bromo-2-methyl-6-(trifluoromethyl)spiro[3,4-dihydropyrrolo[1,2-a]pyrazine-1,4'-piperidine]-1'-carboxylate

HRID 1405360Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1405360
[CH3:1][N:2]1[C:14]2([CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[C:6]2=[CH:7][CH:8]=[C:9]([C:10]([F:13])([F:12])[F:11])[N:5]2[CH2:4][CH2:3]1.C1C(=O)N([Br:34])C(=O)C1>C(#N)C>[Br:34][C:7]1[CH:8]=[C:9]([C:10]([F:11])([F:13])[F:12])[N:5]2[CH2:4][CH2:3][N:2]([CH3:1])[C:14]3([CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)[C:6]=12

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 68153221tert-Butyl 2'-methyl-6'-(trifluoromethyl)-3',4'-dihydro-2'H-spiro[piperidine-4,1'-pyrrolo[1,2-a]pyrazine]-1-carboxylate

Produkt 1

HCID 68153220Tert-butyl 8-bromo-2-methyl-6-(trifluoromethyl)spiro[3,4-dihydropyrrolo[1,2-a]pyrazine-1,4'-piperidine]-1'-carboxylateAusbeute 79,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 2-methyl-6-(trifluoromethyl)spiro[3,4-dihydropyrrolo[1,2-a]pyrazine-1,4′-piperidine]-1′-carboxylate (5.60 g, 15.0 mmol) in acetonitrile (50 mL) was added NBS (2.80 g, 15.8 mmol). The mixture was stirred at room temperature overnight. The solvent was removed and the residue was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over MgSO4 and concentrated to dryness. The crude material was purified by column chromatography (10-20% EtOAc-Hex) to provide tert-butyl 8-bromo-2-methyl-6-(trifluoromethyl)spiro[3,4-dihydropyrrolo[1,2-a]pyrazine-1,4′-piperidine]-1′-carboxylate (5.40 g, 73%) as a light yellow solid. ESI-MS m/z calc. 452.3. found 454.5 (M+1)+; Retention time: 1.60 minutes (3 minute run).

Aufarbeitung

  1. customThe solvent was removed
  2. customthe residue was partitioned between EtOAc and water
  3. extractionThe aqueous layer was extracted with EtOAc (2×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to dryness
  7. customThe crude material was purified by column chromatography (10-20% EtOAc-Hex)

Quellen und Nachweise

ORD-Eintrag
ord-79c61e4026a14b7d8283e01cdbb189cb
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08916565B2

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