Benzyl Bromide → HCID 67421015, compound

HRID 2365924Notes

Reaction equation

HRID 2365924 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([C:20]2[CH:25]=[C:24]([F:26])[C:23]([OH:27])=[CH:22][C:21]=2[OH:28])[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CC(C)=O>[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([C:20]2[CH:25]=[C:24]([F:26])[C:23]([O:27][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:22][C:21]=2[O:28][CH2:17][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 67423480HCID 67423480, compound

Product 1

HCID 67421015HCID 67421015, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

241 mg (1.74 mmol, 3 eq) of potassium carbonate (325 mesh) are added to a solution of 181 mg (0.58 mmol, 1 eq) of 4-(5-fluoro-2,4-dihydroxyphenyl)piperidine-1-carboxylic acid tert-butyl ester in 3 ml of acetone. 152 μl (1.28 mmol, 2.2 eq) of benzyl bromide are added dropwise. The reaction medium is heated at 50° C. for 20 hours. The solvent is evaporated off and then the residue is taken up with a water/ethyl acetate mixture. The aqueous phase is extracted with ethyl acetate, and the organic phases are combined, washed with a solution of sodium hydrogen carbonate and then with a saturated solution of sodium chloride, dried over magnesium sulphate, filtered and evaporated. The residue is chromatographed on silica gel, elution being carried out with 85/15 heptane/ethyl acetate.

Workup

  1. customThe solvent is evaporated off
  2. extractionThe aqueous phase is extracted with ethyl acetate
  3. washwashed with a solution of sodium hydrogen carbonate
  4. dry with materialwith a saturated solution of sodium chloride, dried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is chromatographed on silica gel, elution

Sources & evidence

ORD record
ord-4544f4a949154192b66a67abd7ff92eb
Source dataset
uspto-grants-2014_04
Patent number
US08697726B2

Reaction notes

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