Dichloromethane → 1-[5-Bromo-3-(tert-butyl)-2-methoxyphenyl]-4-piperidinol

HRID 1295962Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1295962
[BH4-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:7]([O:17][CH3:18])=[C:8]([N:10]2[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]2)[CH:9]=1.C(Cl)Cl.C(OCC)(=O)C>CO.O>[Br:3][C:4]1[CH:5]=[C:6]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:7]([O:17][CH3:18])=[C:8]([N:10]2[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]2)[CH:9]=1

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 589099451-[5-Bromo-3-(tert-butyl)-2-methoxyphenyl]-4-piperidinone

Produkt 1

HCID 589100191-[5-Bromo-3-(tert-butyl)-2-methoxyphenyl]-4-piperidinolAusbeute 64,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

NaBH4 (0.23 g, 6.1 mmol) was added to a mixed solution of. 1-[5-bromo-3-(tert-butyl)-2-methoxyphenyl]-4-piperidinone (2.0 g, 5.9 mmol) in methanol (12 ml)-methylene chloride (12 ml) while cooling on ice. After completion of the reaction, the mixture was diluted with water and extraction was performed with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (1.3 g).

Aufarbeitung

  1. customAfter completion of the reaction
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-90802c2995dd48948a7754c1b0d97167
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07244730B2

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