Sodium Bicarbonate → Tert-butyl {1-[(2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)methyl]piperidin-4-yl}carbamate

HRID 1256266Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1256266
[O:1]=[C:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([CH:12]=O)=[CH:7][CH:8]=2)[NH:3]1.[NH:14]1[CH2:19][CH2:18][CH:17]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:16][CH2:15]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[O:1]=[C:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([CH2:12][N:14]3[CH2:15][CH2:16][CH:17]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])[CH2:18][CH2:19]3)=[CH:7][CH:8]=2)[NH:3]1

Komponenten

6

Edukt 4

HCID 516892Sodium BicarbonateHCID 7238334-(N-Boc-amino)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 593980391,2,3,4-Tetrahydro-2-oxo-7-quinolinecarboxaldehyde

Produkt 1

HCID 86655981Tert-butyl {1-[(2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)methyl]piperidin-4-yl}carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A solution of the compound (19.8 g) obtained in Step 1-4 and tert-butyl piperidin-4-ylcarbamate (24.8 g) in CHCl3 (450 mL) was stirred at 70° C. for 1.5 hours and allowed to cool to room temperature. Thereafter, NaBH(OAc)3 (35.9 g) was added to the mixture under ice cooling and the mixture was stirred at room temperature for 12 hours. A saturated aqueous NaHCO3 solution was added to the reaction mixture and then a water layer and an organic layer were separated. The water layer was extracted three times with CHCl3. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel 60 N, mobile phase: MeOH/CHCl3=33/66 to 100/0; v/v) to obtain tert-butyl {1-[(2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)methyl]piperidin-4-yl}carbamate (37.8 g, a colorless solid).

Aufarbeitung

  1. customa water layer and an organic layer were separated
  2. extractionThe water layer was extracted three times with CHCl3
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (silica gel 60 N, mobile phase: MeOH/CHCl3=33/66 to 100/0; v/v)

Quellen und Nachweise

ORD-Eintrag
ord-b36b64334dd64212bbd14935416c2461
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461182B2

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