2,6-Dibromopyridine → tert-Butyl 4-[(6-bromopyridin-2-yl)(hydroxy)methyl]piperazine-1-carboxylate

HRID 385803Notes

Reaction equation

HRID 385803 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.C([Li])CCC.[CH:14]([N:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1)=[O:15]>O1CCCC1>[Br:8][C:4]1[N:3]=[C:2]([CH:14]([OH:15])[N:16]2[CH2:17][CH2:18][N:19]([C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])[CH2:20][CH2:21]2)[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 122742,6-DibromopyridineHCID 205924341-PIPERAZINECARBOXYLIC ACID,4-FORMYL-,1,1-DIMETHYLETHYL ESTERHCID 178418339Butyllithium

Product 1

HCID 59526180tert-Butyl 4-[(6-bromopyridin-2-yl)(hydroxy)methyl]piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2,6-Dibromopyridine (5.45 g, 23.01 mmol) was dissolved in tetrahydrofuran (27.3 mL) and cooled to −78° C. under argon after which n-butyllithium (10.40 mL, 26.0 mmol) was added and the solution was stirred for thirty minutes. A solution of tert-butyl 4-formylpiperazine-1-carboxylate (5.00 g, 23.47 mmol) in tetrahydrofuran (8 mL) was added and the solution was stirred at −78° C. for one hour and then for one hour at ambient temperature. The reaction was quenched with saturated sodium bicarbonate (10 mL) and stirred for ten minutes. The product was extracted with ether, dried over magnesium sulfate, filtered and concentrated. The crude material was purified by silica gel chromatography to give the title compound.

Workup

  1. additionwas added
  2. stirringthe solution was stirred at −78° C. for one hour
  3. customThe reaction was quenched with saturated sodium bicarbonate (10 mL)
  4. stirringstirred for ten minutes
  5. extractionThe product was extracted with ether
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-9bfe0fc00e724814a8966c53875d08af
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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