Anisole → HCID 58155274, compound

HRID 1929493Notes

Reaction equation

HRID 1929493 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@@:8]2([CH3:26])[N:13](CC3C=CC(OC)=CC=3)[C:12](=[O:23])[C:11]([CH3:25])([CH3:24])[O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C1(OC)C=CC=CC=1.FC(F)(F)S(O)(=O)=O.C(=O)([O-])O.[Na+]>FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:3]=[C:4]([C@@:8]2([CH3:26])[NH:13][C:12](=[O:23])[C:11]([CH3:25])([CH3:24])[O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 7519AnisoleHCID 62406Trifluoromethanesulfonic acidHCID 516892Sodium BicarbonateHCID 58155245HCID 58155245, compound

Product 1

HCID 58155274HCID 58155274, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
73 °C

Procedure

A solution of (R)-5-(3-bromo-phenyl)-4-(4-methoxy-benzyl)-2,2,5-trimethyl-morpholin-3-one (487 mg, 1.2 mmol) and anisole (2.305 g, 21.3 mmol) in trifluoroacetic acid (6 ml) was treated dropwise with trifluoromethanesulfonic acid (1.19 ml). After complete addition, the violet reaction mixture was heated at 73° C. for 23 hours. The cooled reaction mixture was poured into a saturated solution of sodium hydrogen-carbonate which was extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over sodium sulfate, and evaporated at reduced pressure. The crude product was purified by chromatography on silica gel using a gradient of heptane and ethyl acetate=100/0 to 66/34 as the eluent. The product containing fractions (550 mg, orange foam) were collected and engaged in the next step without further purification and characterization.

Workup

  1. additionAfter complete addition
  2. customThe cooled reaction mixture
  3. extractionwas extracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated at reduced pressure
  8. customThe crude product was purified by chromatography on silica gel using a gradient of heptane and ethyl acetate=100/0 to 66/34 as the eluent
  9. additionThe product containing fractions (550 mg, orange foam)
  10. customwere collected
  11. customengaged in the next step without further purification and characterization

Sources & evidence

ORD record
ord-f6d0572062204153ab894cd56e1f092f
Source dataset
uspto-grants-2012_05
Patent number
US08188079B2

Reaction notes

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