m-Xylyl bromide → HCID 54555641, compound

HRID 1739011Notes

Reaction equation

HRID 1739011 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:12](=[O:21])[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26]Br>CN(C)C=O>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][C:13]([CH2:22][C:23]2[CH:30]=[CH:29][CH:28]=[C:25]([CH3:26])[CH:24]=2)([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:12](=[O:21])[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 12099m-Xylyl bromideHCID 24758Sodium hydrideHCID 158529891-tert-Butyl 4-ethyl 3-oxopiperidine-1,4-dicarboxylate

Product 1

HCID 54555641HCID 54555641, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) slurry of sodium hydride (0.29 g, 12 mmol) in anhydrous dimethylformamide (50 mL), a solution of ethyl N-tert-butoxycarbonyl-3-oxo-piperidine-4-carboxylate (2.73 g, 10 mmol) in DMF (10 mL) was added. The mixture was stirred at 0° C. for 30 min., and at room temp. for 30 min. The resultant solution was cooled back to 0° C. and treated with 3-methylbenzyl bromide (1.63 mL, 12 mmol). The reaction mixture was stirred at room temp. overnight and concentrated under vacuum. The residue was partitioned between ethyl acetate and aqueous sodium bicarbonate. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 17.5% ethyl acetate in hexane. Collection and concentration of appropriate fractions provided the title compound.

Workup

  1. waitat room temp. for 30 min
  2. stirringThe reaction mixture was stirred at room temp. overnight
  3. concentrationconcentrated under vacuum
  4. customThe residue was partitioned between ethyl acetate and aqueous sodium bicarbonate
  5. extractionThe organic extract
  6. washwas washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-49ead2d6fee54f02a72f4df7869bc72f
Source dataset
uspto-grants-1999_10
Patent number
US05965578

Reaction notes

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