Sodium Bicarbonate → (7-(1-(4-Isopropylphenyl)vinyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)amine

HRID 1787203Notes

Reaction equation

HRID 1787203 reaction equation
O[C:2]([C:13]1[C:21]2[O:20][CH2:19][CH2:18][C:17]=2[C:16]([CH3:22])=[C:15]([NH:23]C(=O)OC(C)(C)C)[C:14]=1[CH3:31])([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:12])[CH3:11])=[CH:6][CH:5]=1)[CH3:3].Cl.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[CH:10]([C:7]1[CH:8]=[CH:9][C:4]([C:2]([C:13]2[C:21]3[O:20][CH2:19][CH2:18][C:17]=3[C:16]([CH3:22])=[C:15]([NH2:23])[C:14]=2[CH3:31])=[CH2:3])=[CH:5][CH:6]=1)([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21866389Hydrogen chloride-ethyl acetateHCID 86612348Tert-butyl(7-(1-hydroxy-1-(4-isopropylphenyl)ethyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)carbamate

Product 1

HCID 23114152(7-(1-(4-Isopropylphenyl)vinyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)amineYield 99.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl (7-(1-hydroxy-1-(4-isopropylphenyl)ethyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)carbamate obtained in Example 223 (306 mg, 0.72 mmol) in ethyl acetate (5 mL) was added dropwise a solution of 4 N hydrochloric acid-ethyl acetate (5 mL) under ice-cooling, and the reaction solution was stirred for 30 minutes. The reaction solution was added to a saturated sodium hydrogen carbonate solution, which was extracted with ethyl acetate. The combined organic layer was washed with a saturated sodium hydrogen carbonate solution and a saturated brine, dried over anhydrous sodium sulfate, filtered and then concentrated under reduced pressure to obtain 221 mg (yield: quantitative) of the title compound. Oily matter.

Workup

  1. temperaturecooling
  2. extractionwas extracted with ethyl acetate
  3. washThe combined organic layer was washed with a saturated sodium hydrogen carbonate solution
  4. dry with materiala saturated brine, dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-27a16d3093b34616b0498885dd16cae1
Source dataset
uspto-grants-2009_03
Patent number
US07507841B2

Reaction notes

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