Ethyl Acetate → 5-cinnamoyl-3-isobutyl-3-phenyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one

HRID 1747739Notes

Reaction equation

HRID 1747739 reaction equation
[CH2:1]([C:5]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH2:10][NH:11][CH2:12][CH2:13][C:8]=2[C:7](=[O:14])[O:6]1)[CH:2]([CH3:4])[CH3:3].[CH:21](=[O:30])/[CH:22]=[CH:23]/[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(OCC)(=O)C>C1COCC1>[C:21]([N:11]1[CH2:12][CH2:13][C:8]2[C:7](=[O:14])[O:6][C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:9]=2[CH2:10]1)(=[O:30])[CH:22]=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 637511CinnamaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 896147743-isobutyl-3-phenyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one

Product 1

HCID 781324195-cinnamoyl-3-isobutyl-3-phenyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-oneYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-isobutyl-3-phenyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one (50 mg, 0.184 mmol) in THF (5 mL) was added trans-cinnamaldehyde (49 mg, 0.369 mmol) and the reaction mixture stirred at room temperature for 1 hour. Sodium triacetoxyborohydride (117 mg, 0.553 mmol) was added and the reaction mixture stirred at room temperature for additional 2 hours. Ethyl acetate (10 mL) was added and the organic solution washed with sat. NaHCO3 (10 mL), brine (10 mL), dried (MgSO4), and concentrated. The residue was purified by column chromatography (12 g, SiO2, 0 to 20% ethyl acetate in hexanes) to provide 5-cinnamoyl-3-isobutyl-3-phenyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one (45 mg, 63%) as a white solid: 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 0.73-1.05 (m, 6H), 1.54-1.84 (m, 2H), 2.20-2.48 (m, 3H), 2.52-2.66 (m, 1H), 2.73-2.89 (m, 1H), 2.99-3.14 (m, 1H), 3.19-3.37 (m, 2H), 3.43 (d, J=17.71 Hz, 1H), 6.23 (dt, J=15.82, 6.59 Hz, 1H), 6.44-6.57 (m, 1H), 7.20-7.46 (m, 10H); MS m/z 388 (M+H)+, 410 (M+23)+, 386 (M−H)−.

Workup

  1. stirringthe reaction mixture stirred at room temperature for additional 2 hours
  2. washthe organic solution washed with sat. NaHCO3 (10 mL), brine (10 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (12 g, SiO2, 0 to 20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-855d3b7690334b5b8a4b92786e21b068
Source dataset
uspto-grants-2015_10
Patent number
US09150582B2

Reaction notes

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