Benzyl Bromide → HCID 71268696, compound

HRID 70778Notes

Reaction equation

HRID 70778 reaction equation
[H-].[Na+].[OH:3][CH2:4][C:5]1[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH:10]=1.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[CH2:18]([O:3][CH2:4][C:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH:6]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 225944841,1-Dimethylethyl 3,6-dihydro-4-(hydroxymethyl)-1(2H)-pyridinecarboxylate

Product 1

HCID 71268696HCID 71268696, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

55% sodium hydride (1.30 g) was added under ice-cooling to a THF (87 ml) solution of tert-butyl 4-(hydroxymethyl)-3,6-dihydropyridine-1(2H)-carboxylate (5.77 g), and this suspension was stirred at room temperature for 30 minutes. After ice-cooling again, benzyl bromide (5.32 g) and tetrabutylammonium iodide (1.00 g) were added thereto and stirring was performed at room temperature for 3 hours. After adding a saturated ammonium chloride aqueous solution, extraction was performed with EtOAc. A residue which was obtained by washing with saturated brine, drying over anhydrous magnesium sulfate, and concentration was purified by silica gel column chromatography (EtOAc/hexane) to obtain tert-butyl 4-[(benzyloxy)methyl]-3,6-dihydropyridine-1(2H)-carboxylate (6.16 g).

Workup

  1. temperatureAfter ice-cooling again
  2. stirringstirring
  3. waitwas performed at room temperature for 3 hours
  4. additionAfter adding
  5. extractiona saturated ammonium chloride aqueous solution, extraction
  6. customA residue which was obtained
  7. washby washing with saturated brine
  8. dry with materialdrying over anhydrous magnesium sulfate, and concentration
  9. customwas purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-416bc3a3d2684821b8df0a95b0610b11
Source dataset
uspto-grants-2014_09
Patent number
US08822688B2

Reaction notes

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