HCID 11747380, compound → HCID 15336556, compound

HRID 1078260Notes

Reaction equation

HRID 1078260 reaction equation
[CH2:1]([CH:4]1[C:13]2[N:12]=[C:11]([O:14][CH3:15])[CH:10]=[CH:9][C:8]=2[CH2:7][C:6]2([O:19][CH2:18][CH2:17][O:16]2)[CH2:5]1)[CH:2]=[CH2:3].[H][H]>CCO.[Pd]>[CH3:15][O:14][C:11]1[CH:10]=[CH:9][C:8]2[CH2:7][C:6]3([O:19][CH2:18][CH2:17][O:16]3)[CH2:5][CH:4]([CH2:1][CH2:2][CH3:3])[C:13]=2[N:12]=1

Participants

5

Reactant 2

HCID 11747380HCID 11747380, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15336556HCID 15336556, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 4a (1.04 g, 4 mmol) in 100 mL of EtOH was hydrogenated at 60 psi hydrogen pressure (Parr shaker) over 200 mg of 5% Pd/C for 5 h. Filtration, concentration, and flash chromatography of the residue (30% ethyl acetate in hexanes) gave 1.03 g (98%) of 4d: IR (neat) 2955, 1599, 1477, 1084, 1031 cm-1 ; 1H NMR δ7.20 (d, 1H, J=8.3 Hz), 6.50 (d, 1H, J=8.3 Hz), 4.01 (m, 4H), 3.89 (s, 3H), 2.98 (m, 2H), 2.78 (dd, 1H, J=16.0, 2.4 Hz), 2.01 (m, 2H), 1.67 (m, 2H), 1.40 (m, 2H), 0.96 (t, 3H, J=7.2 Hz); 13C NMR δ162.0, 155.7, 139.6, 121.3, 107.9, 107.7, 64.4, 53.0, 39.5, 38.0, 37.2, 35.9, 19.9, 14.3; MS m/z 263 (M+).

Workup

  1. filtrationFiltration, concentration, and flash chromatography of the residue (30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-3e4cdf2de4d5448da967afbd71175507
Source dataset
uspto-grants-1996_08
Patent number
US05547960

Reaction notes

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