Tetrahydrofuran → HCID 59255084, compound

HRID 1691172Notes

Reaction equation

HRID 1691172 reaction equation
O1CCCC1.[N:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH2:13][C:14]1[CH:23]=[CH:22][C:17]([C:18](OC)=[O:19])=[CH:16][CH:15]=1.[H-].C([NH2+]CC(C)C)C(C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C(OCC)(=O)C>[N:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:18][OH:19])=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 9855836Potassium sodium tartarateHCID 21898182Diisobutylammonium hydrideHCID 59255391Methyl 4-(2-pyridin-2-yl-ethyl)benzoate

Product 1

HCID 59255084HCID 59255084, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To an anhydrous tetrahydrofuran (50 mL) solution of methyl 4-(2-pyridin-2-yl-ethyl)benzoate (3.71 g, 15.4 mmol) described in Manufacturing Example 93-1-3 was added diisobutyl ammonium hydride (0.97 M toluene solution, 39.7 mL, 38.5 mmol) on a dry ice-ethanol bath (−78° C.) under nitrogen atmosphere. After 30 minutes of stirring, 15% aqueous potassium sodium tartrate solution (100 mL) was added to the reaction mixture, and stirred for 30 minutes at room temperature. Ethyl acetate (100 mL) was added, and the organic layer and water layer were separated. The organic layer was washed with water and saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure to obtain the title compound (3.16 g, 96%).

Workup

  1. stirringstirred for 30 minutes at room temperature
  2. customthe organic layer and water layer were separated
  3. washThe organic layer was washed with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-7599538cf25a4a7e9804a2ff6f502b44
Source dataset
uspto-grants-2012_04
Patent number
US08153662B2

Reaction notes

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