tert-Butyl 4-oxopiperidine-1-carboxylate → 5-fluoro-1-(piperidin-4-yl)-2,3-dihydro-1H-indole

HRID 45583

Reaktionsgleichung

Reaktionsgleichung von HRID 45583
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2.C([N:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1)(OC(C)(C)C)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O.C(=O)(O)[O-].[Na+]>O1CCCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:21]1[CH2:22][CH2:23][NH:18][CH2:19][CH2:20]1)[CH2:6][CH2:5]2

Komponenten

7

Edukt 4

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 27744635-FluoroindolineHCID 5049666Sodium triacetoxyborohydrideHCID 86585896Sodium bicarbonate water

Produkt 1

HCID 674178425-fluoro-1-(piperidin-4-yl)-2,3-dihydro-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 5-fluoroindoline (1.0 g, 7.30 mmol) and N-Boc-4-piperidone (1.60 g, 7.50 mmol) in tetrahydrofuran (10.0 mL) was added sodium triacetoxyborohydride (1.80 g, 7.50 mmol). After stirring for 3 hours at room temperature, to the mixture were added saturated sodium bicarbonate water and ethyl acetate, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified with silica gel column (chloroform/methanol=98/2 to 90/10) to give a Boc derivative of the title compound. MS (ESI+) 321 (M++1, 100%)

Aufarbeitung

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified with silica gel column (chloroform/methanol=98/2 to 90/10)

Quellen und Nachweise

ORD-Eintrag
ord-e200522c45314eee9bac792acc4c12d9
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541585B2

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