HCID 53704167, compound → HCID 54009818, compound

HRID 399426Notes

Reaction equation

HRID 399426 reaction equation
[OH:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:17])([C:14]([NH2:16])=O)[CH2:6][CH2:5]2>C1COCC1.Cl>[NH2:16][CH2:14][C:7]1([CH3:17])[CH2:6][CH2:5][C:4]2[C:9](=[C:10]([CH3:13])[C:11]([CH3:12])=[C:2]([OH:1])[C:3]=2[CH3:18])[O:8]1

Participants

4

Reactant 1

HCID 53704167HCID 53704167, compound

Product 1

HCID 54009818HCID 54009818, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxamide (1.0 g, 4.0 mmol) in THF (30 mL) was added boranemethyl sulfide complex (10 M, 1.9 mL, 19 mmol). The resultant mixture was refluxed for 7 h. To the resultant reaction mixture was added IN hydrochloric acid (9.6 mL) under ice-cooling, and the resultant mixture was further refluxed for 2 h followed by concentration under reduced pressure. The residue was extracted with ethyl acetate after addition of 1N aqueous solution of sodium hydroxide. The organic layer was washed with 10% aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by silica-gel column chromatography to give an amine, 2-aminomethyl-6-hydroxy-2,5,7,8-tetramethylchroman (yield 55%).

Workup

  1. customTo the resultant reaction mixture
  2. temperaturecooling
  3. concentrationfollowed by concentration under reduced pressure
  4. extractionThe residue was extracted with ethyl acetate
  5. additionafter addition of 1N aqueous solution of sodium hydroxide
  6. washThe organic layer was washed with 10% aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. custompurified by silica-gel column chromatography

Sources & evidence

ORD record
ord-d1c9ca7d65c542b8be9b62ff17bc90a1
Source dataset
uspto-grants-1998_10
Patent number
US05821247

Reaction notes

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