Ammonium Acetate → 4,5,6,7-Tetrahydro-1-benzofuran-4-amine

HRID 1612155

Reaction equation

HRID 1612155 reaction equation
[O:1]1[C:5]2[CH2:6][CH2:7][CH2:8][C:9](=O)[C:4]=2[CH:3]=[CH:2]1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:17].[Na+]>CO>[O:1]1[C:5]2[CH2:6][CH2:7][CH2:8][CH:9]([NH2:17])[C:4]=2[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 27335414,5,6,7-Tetrahydro-1-benzofuran-4-oneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 185251714,5,6,7-Tetrahydro-1-benzofuran-4-amineYield 38%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6,7-dihydro-1-benzofuran-4(5H)-one (2.0 g) in methanol (50 ml) was added 3 Å sieves (15 g), ammonium acetate (11.3 g) and sodium cyanoborohydride (1.22 g). After 48 h of stirring, the reaction mixture was filtered through celite, concentrated, dissolved in 1 N HCl (100 ml) and washed with ethyl ether (3×100 ml). The Aqueous layer was basified to pH 10 (NaOH), extracted methylene chloride (3×100 ml), dried MgSO4, filtered and concentrated to yield (760 mg, 38%) of the title compound as an oil:

Workup

  1. filtrationthe reaction mixture was filtered through celite
  2. concentrationconcentrated
  3. dissolutiondissolved in 1 N HCl (100 ml)
  4. washwashed with ethyl ether (3×100 ml)
  5. extractionextracted methylene chloride (3×100 ml), dried MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3f6bba7a59fd4951a184dd8095483adf
Source dataset
uspto-grants-2006_01
Patent number
US06992087B2

Linked notes

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