Hydrochloric Acid → HCID 58155211, compound

HRID 1929487Notes

Reaction equation

HRID 1929487 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:19])=[C:6]([C@:8]([NH:14][C:15](=[O:18])[CH2:16]Cl)([CH3:13])[C:9]([OH:12])([CH3:11])[CH3:10])[CH:7]=1.[K].Cl>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:19])=[C:6]([C@@:8]2([CH3:13])[NH:14][C:15](=[O:18])[CH2:16][O:12][C:9]2([CH3:11])[CH3:10])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5462222PotassiumHCID 66931584HCID 66931584, compound

Product 1

HCID 58155211HCID 58155211, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
23 °C

Procedure

A dispersion of N-[(R)-1-(5-bromo-2-fluoro-phenyl)-2-hydroxy-1,2-dimethyl-propyl]-2-chloro-acetamide (2.79 g, 7.91 mmol) in toluene (80 ml) at 23° C. was treated dropwise with a solution of potassium amylate (1.7 M in toluene, 24 ml, 41 mmol) within 30 minutes (slightly exothermic reaction). After complete addition the mixture was stirred at 23° C. for 45 minutes. For the workup, the reaction mixture was poured into hydrochloric acid (1M) and extracted with ethyl acetate. The organic layer was separated and washed with a saturated sodium hydrogen-carbonate solution and brine. The combined aqueous layers were re-extracted twice with ethyl acetate. The combined organic layers were dried over sodium sulfate, then evaporated at reduced pressure to yield light brown oil. The crude product was purified by chromatography on silica gel using a gradient of heptane and ethyl acetate as the eluent. The (R)-5-(5-bromo-2-fluoro-phenyl)-5,6,6-trimethyl-morpholin-3-one was obtained as a light yellow gum (1.83 g, 73% of theory). Mass (calculated) C13H15BrFNO2 [316.168]; (found) [M+H]+=316, [M+2-H]+=318.

Workup

  1. customwithin 30 minutes
  2. customslightly exothermic reaction)
  3. additionAfter complete addition the mixture
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with a saturated sodium hydrogen-carbonate solution and brine
  7. extractionThe combined aqueous layers were re-extracted twice with ethyl acetate
  8. dry with materialThe combined organic layers were dried over sodium sulfate
  9. customevaporated at reduced pressure
  10. customto yield light brown oil
  11. customThe crude product was purified by chromatography on silica gel using a gradient of heptane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-5d188f30341949e99314b8a61c201527
Source dataset
uspto-grants-2012_05
Patent number
US08188079B2

Reaction notes

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