HCID 71610394, compound → HCID 71610395, compound

HRID 1747734Notes

Reaction equation

HRID 1747734 reaction equation
[CH2:1]([C:5]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:9]2[CH2:10][N:11]([C:14](=[O:26])/[CH:15]=[CH:16]/[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N+:23]([O-])=O)[CH2:12][CH2:13][C:8]=2[C:7](=[O:27])[O:6]1)[CH:2]([CH3:4])[CH3:3]>C(O)C.C(OCC)(=O)C.[Pd]>[NH2:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][CH2:15][C:14]([N:11]1[CH2:12][CH2:13][C:8]2[C:7](=[O:27])[O:6][C:5]([CH2:1][CH:2]([CH3:3])[CH3:4])([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:9]=2[CH2:10]1)=[O:26]

Participants

4

Reactant 1

HCID 71610394HCID 71610394, compound

Product 1

HCID 71610395HCID 71610395, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

To a solution of (E)-3-isobutyl-5-(3-(2-nitrophenyl)acryloyl)-3-phenyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one (90 mg, 0.20 mmol) in ethanol/ethyl acetate/(3:1, 20 mL) was added Pd/C (10%, 20 mg). The reaction mixture was stirred vigorously under an atmosphere of H2(g) at room temperature for 1 h. The mixture was filtered through a pad of diatomaceous earth, the filtrate concentrated in vacuo, and the residue purified by column chromatography (4 g, SiO2, 0 to 50% ethyl acetate in hexanes) to provide 5-(3-(2-aminophenyl)propanoyl)-3-isobutyl-3-phenyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one (54 mg, 64%): 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 0.82-0.98 (m, 6H), 1.59-1.71 (m, 1H), 1.73-1.87 (m, 1H), 2.18-2.37 (m, 2H), 2.72 (d, J=6.78 Hz, 2H), 2.87 (d, J=6.78 Hz, 2H), 3.22-3.33 (m, 1H), 3.46-3.66 (m, 2H), 3.77-3.89 (m, 2H), 3.92-4.04 (m, 1H), 4.60-4.74 (m, 1H), 6.59-6.64 (m, 2H), 6.96-7.07 (m, 2H), 7.28-7.44 (m, 5H); MS m/z 419 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a pad of diatomaceous earth
  2. concentrationthe filtrate concentrated in vacuo
  3. customthe residue purified by column chromatography (4 g, SiO2, 0 to 50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-66a6376916fd41d69618757f22ee8869
Source dataset
uspto-grants-2015_10
Patent number
US09150582B2

Reaction notes

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