Sodium borohydride → Tert-butyl 4-[5-bromo-3-(hydroxymethyl)pyridin-2-yl]piperazine-1-carboxylate

HRID 2403605Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2403605
[Br:1][C:2]1[CH:3]=[C:4]([CH:21]=[O:22])[C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH2:21][OH:22])[C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 86667973Tert-butyl 4-(5-bromo-3-formylpyridin-2-yl)piperazine-1-carboxylate

Produkt 1

HCID 68107347Tert-butyl 4-[5-bromo-3-(hydroxymethyl)pyridin-2-yl]piperazine-1-carboxylateAusbeute 91,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a mixture of tert-butyl 4-(5-bromo-3-formylpyridin-2-yl)piperazine-1-carboxylate (1 g) and MeOH (20 ml) was added sodium borohydride (153 mg). After stirring at room temperature for 2 hours, the solvent was evaporated under reduced pressure. To the obtained residue was added water, followed by extraction with EtOAc. The organic layer was dried over MgSO4, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain tert-butyl 4-[5-bromo-3-(hydroxymethyl)pyridin-2-yl]piperazine-1-carboxylate (922 mg).

Aufarbeitung

  1. customthe solvent was evaporated under reduced pressure
  2. additionTo the obtained residue was added water
  3. extractionfollowed by extraction with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-28a9f422bc034dd9b795f3e0b9308502
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08802679B2

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