Hydrochloric Acid → HCID 54009818, compound

HRID 1417711Notes

Reaction equation

HRID 1417711 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.Cl>C1COCC1>[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 2

HCID 313Hydrochloric AcidHCID 53704167HCID 53704167, compound

Product 1

HCID 54009818HCID 54009818, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 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 borane-methyl sulfide complex (10M, 1.9 mL, 19 mmol). The resultant mixture was refluxed for 7 h. To the resultant reaction mixture was added 1N 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-172330b182124d06a5f069b8d0eafb76
Source dataset
uspto-grants-1999_03
Patent number
US05877318

Reaction notes

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