Sodium Carbonate → Tert-butyl 4-(6-fluoroindolin-1-yl)piperidine-1-carboxylate

HRID 591345

Reaktionsgleichung

Reaktionsgleichung von HRID 591345
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][NH:8]2)=[CH:4][CH:3]=1.[C:11]([N:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[CH:21]2[CH2:22][CH2:23][N:18]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:19][CH2:20]2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 10340Sodium CarbonateHCID 2604006-fluoro-2,3-dihydro-1H-indoleHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 89613009Tert-butyl 4-(6-fluoroindolin-1-yl)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 6-fluoroindoline (9.36 g, 68 mmol) in CH2Cl2 (100 mL) was added 1-Boc-4-piperidone (13.6 g, 68 mmol). The resulting mixture was stirred at room temperature for 1 h and NaBH(OAc)3 (18 g, 85 mmol, 1.25 equiv) was added. The resulting mixture was stirred at room temperature for 24 h and was then poured slowly to a vigorously stirred Na2CO3(aq). After 30 min stirring, the layers were separated. The aqueous layer was extracted with CH2Cl2 (100 mL). The combined organic layer was washed with brine (100 mL), dried (Na2SO4), and filtered. The solvent was removed by roto-evaporator, Et2O (10 mL) and then hexane (150 mL) were added to the resulting residue. The mixture was allowed to stand, resulting in the formation of a white solid, which was collected and washed with 5% Et2O/hexane and then dried. This was repeated to yield three crops of tert-butyl 4-(6-fluoroindolin-1-yl)piperidine-1-carboxylate as a white solid.

Aufarbeitung

  1. stirringThe resulting mixture was stirred at room temperature for 24 h
  2. stirringAfter 30 min stirring
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with CH2Cl2 (100 mL)
  5. washThe combined organic layer was washed with brine (100 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customThe solvent was removed by roto-evaporator, Et2O (10 mL)
  9. additionhexane (150 mL) were added to the resulting residue
  10. customresulting in the formation of a white solid, which
  11. customwas collected
  12. washwashed with 5% Et2O/hexane
  13. customdried

Quellen und Nachweise

ORD-Eintrag
ord-b2d5a6cb376e42f7ab91332e28db0afd
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238658B2

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