Acetic Acid → HCID 67165602, compound

HRID 553290Notes

Reaction equation

HRID 553290 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]=O)[CH:12]=2)=[CH:7][CH:6]=1.C(O)(=O)C.[CH2:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][NH:25]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][N:25]3[CH2:26][C:27]4[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:24]3)[CH:12]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 422478IsoindolineHCID 5049666Sodium triacetoxyborohydrideHCID 86628374HCID 86628374, compound

Product 1

HCID 67165602HCID 67165602, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(3′-Formyl-biphenyl-4-yl)-acetic acid methyl ester (1.22 g), acetic acid (0.23 mL) and iso-indoline (0.48 g) were combined in methanol (10 mL). After 1 hour, sodium triacetoxyborohydride (1.27 g) was added and stirred for 18 hours, at room temperature, under nitrogen. The reaction was quenched with 0.880 ammonia solution and concentrated. The residue was dissolved in methanol and loaded onto a conditioned SCX cartridge (50 g Varian). The cartridge was washed with methanol (3×50 mL), then eluted with methanolic ammonia solution (2×50 mL) and the combined elution fractions evaporated. Purification on silica, eluting with triethylamine/ethyl acetate/iso-hexane [1:19:80], to give the subtitle compound as a dark brown oil (450 mg).

Workup

  1. customThe reaction was quenched with 0.880 ammonia solution
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in methanol
  4. washThe cartridge was washed with methanol (3×50 mL)
  5. washeluted with methanolic ammonia solution (2×50 mL)
  6. washthe combined elution fractions
  7. customevaporated
  8. customPurification on silica
  9. washeluting with triethylamine/ethyl acetate/iso-hexane [1:19:80]

Sources & evidence

ORD record
ord-11163607474d4fae89a51846f9705c58
Source dataset
uspto-grants-2011_05
Patent number
US07951954B2

Reaction notes

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