Benzyl Bromide → HCID 68832696, compound

HRID 2109864Notes

Reaction equation

HRID 2109864 reaction equation
[C:1]([N:4]1[CH:10]2[CH:8]([CH:9]2[CH2:11][OH:12])[N:7]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:6](=[O:21])[CH2:5]1)(=[O:3])[CH3:2].[H-].[Na+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1COCC1>[C:1]([N:4]1[CH:10]2[CH:8]([CH:9]2[CH2:11][O:12][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:7]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=2)[C:6](=[O:21])[CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 68832620HCID 68832620, compound

Product 1

HCID 68832696HCID 68832696, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-acetyl-2-(4-fluorobenzyl)-7-(hydroxymethyl)-2,5-diazabicyclo[4.1.0]heptane-3-one (1.3 g, 4.45 mmol) in 40 mL anhydrous THF under nitrogen, sodium hydride (60% in mineral oil, 231 mg, 5.78 mmol) was added. After stirring for 1 h, benzyl bromide (0.58 ml, 4.89 mmol) in THF (1 mL) was added. The reaction mixture was stirred at room temperature overnight. The reaction was quenched with saturated aqueous ammonium chloride solution. The aqueous layer was extracted with chloroform three times. The combined organic phases were dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel using hexanes and ethyl acetate as eluents to give the title product.

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. customThe reaction was quenched with saturated aqueous ammonium chloride solution
  3. extractionThe aqueous layer was extracted with chloroform three times
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-1e04fd4c9ec1490da2a3faeb3a07d95c
Source dataset
uspto-grants-2009_04
Patent number
US07517532B2

Reaction notes

Loading…