Tetrahydrofuran → 6-[(1E)-3-hydroxyprop-1-en-1-yl]-2-isobutyl-4-(4-methylphenyl)quinoline-3-carbonitrile

HRID 1986505Notes

Reaction equation

HRID 1986505 reaction equation
[CH2:1]([C:5]1[C:14]([C:15]#[N:16])=[C:13]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10](/[CH:24]=[CH:25]/[CH:26]=[O:27])[CH:11]=2)[N:6]=1)[CH:2]([CH3:4])[CH3:3].O1CCCC1.[BH4-].[Na+].[Cl-].[NH4+]>CO>[OH:27][CH2:26]/[CH:25]=[CH:24]/[C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[N:6]=[C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[C:14]([C:15]#[N:16])=[C:13]2[C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 51050345HCID 51050345, compound

Product 1

HCID 688291196-[(1E)-3-hydroxyprop-1-en-1-yl]-2-isobutyl-4-(4-methylphenyl)quinoline-3-carbonitrileYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-isobutyl-4-(4-methylphenyl)-6-[(1E)-3-oxoprop-1-en-1-yl]quinoline-3-carbonitrile (4.04 g, 11.4 mmol) in methanol (30 ml)-tetrahydrofuran (30 ml) was added sodium borohydride (216 mg, 5.69 mmol) at 0° C. and the mixture was stirred at room temperature for 10 min. Saturated aqueous ammonium chloride solution was added to the reaction mixture and the mixture was extracted 3 times with ethyl acetate. The combined organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give 6-[(1E)-3-hydroxyprop-1-en-1-yl]-2-isobutyl-4-(4-methylphenyl)quinoline-3-carbonitrile (3.08 g, yield 76%) as yellow crystals. Subsequently, tert-butyl {[6-(3-hydroxypropyl)-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methyl}carbamate was synthesized by a method similar to the method shown in Example 39(1).

Workup

  1. extractionthe mixture was extracted 3 times with ethyl acetate
  2. washThe combined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-03786186e054427a8f38d2ca3b071462
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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