Acetic Acid → HCID 23157599, compound

HRID 508081Notes

Reaction equation

HRID 508081 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[C:14](=O)[CH2:13][CH2:12]2.[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([O:30]C)=[O:29])=[CH:22][CH:21]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O.[OH-].[Li+].Cl>ClCCCl.O.CO>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[CH:14]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:22][CH:21]=1)[CH2:13][CH2:12]2

Participants

10

Reactant 6

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 417374Methyl 3-(4-aminophenyl)propanoateHCID 5049666Sodium triacetoxyborohydrideHCID 23157183HCID 23157183, compound

Product 1

HCID 23157599HCID 23157599, compoundYield 37%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

5-(2,6-Dimethylphenyl)indan-1-one (690 mg, 2.92 mmol), methyl 3-(4-aminophenyl)propanoate (937 mg, 4.09 mmol) and acetic acid (526 mg, 8.76 mmol) were dissolved in 1,2-dichloroethane (20 mL), sodium triacetoxyborohydride (1.86 g, 8.76 mmol) was added by small portions at room temperature, and the mixture was stirred at room temperature for 16 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5%-40% ethyl acetate/hexane). The obtained oil was dissolved in tetrahydrofuran (10 mL), methanol (6 mL), and water (6 mL), and lithium hydroxide monohydrate (133 mg, 3.18 mmol) was added. The mixture was stirred at room temperature for 3 hr. The reaction mixture was neutralized with 1 M hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (10%-60% ethyl acetate/hexane) to give the title compound (414 mg, yield 37%) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (5%-40% ethyl acetate/hexane)
  6. dissolutionThe obtained oil was dissolved in tetrahydrofuran (10 mL)
  7. stirringThe mixture was stirred at room temperature for 3 hr
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe organic layer was washed with saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customthe solvent was evaporated under reduced pressure
  12. customThe residue was purified by silica gel column chromatography (10%-60% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b0379c9063ba4f8796fab284d329f3d0
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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