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

HRID 2403605Notes

Reaction equation

HRID 2403605 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 68107347Tert-butyl 4-[5-bromo-3-(hydroxymethyl)pyridin-2-yl]piperazine-1-carboxylateYield 91.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-28a9f422bc034dd9b795f3e0b9308502
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

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