Water → Tert-butyl 4-(4-formylphenyl)piperidine-1-carboxylate

HRID 2366479Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2366479
CON(C)[C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1.ClCCl>[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17]2)=[CH:8][CH:7]=1)=[O:5]

Komponenten

7

Edukt 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86613864Tert butyl 4-(4-(methoxy(methyl)carbamoyl)phenyl)piperidine-1-carboxylate

Produkt 1

HCID 11254770Tert-butyl 4-(4-formylphenyl)piperidine-1-carboxylateAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of EXAMPLE 88A (0.8 g, 2.3 mmol) in tetrahydrofuran (5 mL) was cooled to −78° C. and treated with lithium aluminum hydride (0.25 g, 6.6 mmol). The mixture was stirred for 30 minutes and treated with water (1 mL) and 15% sodium hydroxide (0.25 mL). Dichloromethane was added and the mixture dried over magnesium sulfate and filtered through silica gel. The solution was concentrated and purified by flash chromatography on silica gel using 1:1 hexane/ethyl acetate to provide the title compound (0.18 g).

Aufarbeitung

  1. dry with materialthe mixture dried over magnesium sulfate
  2. filtrationfiltered through silica gel
  3. concentrationThe solution was concentrated
  4. custompurified by flash chromatography on silica gel using 1:1 hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-0099c68ad03942ffbe6e7e8c54579c00
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697736B2

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