[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][CH2:9][N:8]([CH2:12][C:13]#[N:14])[C:7]=2[CH:15]=1.[C:16]([O-])(=[O:18])[CH3:17].[Na+]>C(OC(=O)C)(=O)C.[Ni].O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][NH:14][C:16](=[O:18])[CH3:17])[C:7]=2[CH:15]=1The compound obtained in Step E (590 mg; 2.88 mmol) is dissolved in a Parr reactor with acetic anhydride. Raney nickel (10% by weight, 60 mg) and sodium acetate (1.5 eq.; 4.33 mmol; 355 mg) are then added. The mixture is left for 12 hours at 50° C. under a hydrogen pressure of 40 psi. After returning to ambient temperature, the solution is filtered over Celite and the filtrate is evaporated. The residue obtained is taken up in water and then extracted three times with ethyl acetate. The organic phases are combined, dried over MgSO4, and then concentrated under reduced pressure. The crude reaction product is purified by flash chromatography on silica gel (eluant: PE/AcOEt (4/6) then AcOEt/MeOH (95/5)). The title product is obtained in the form of white crystals after washing with ether.
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