[CH2:1]([O:8][CH:9]1[CH2:14][C:13]([CH3:16])([CH3:15])[N:12]([OH:17])[C:11]([CH3:19])([CH3:18])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S([O-])([O-])(=O)=O.[Mg+2].CC(C)([O-])C.[K+].[C:32]([O:36][CH3:37])(=[O:35])[CH:33]=[CH2:34]>[Pd].O1CCCC1>[CH2:1]([O:8][CH:9]1[CH2:14][C:13]([CH3:15])([CH3:16])[N:12]([O:17][CH2:34][CH2:33][C:32]([O:36][CH3:37])=[O:35])[C:11]([CH3:19])([CH3:18])[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
A mixture of 20.0 grams (76 mmol) of 4-benzyloxyl-oxyl-2,2,6,6-tetramethylpiperidine, 10.0 grams of anhydrous magnesium sulfate, 500 mg of 5% palladium on carbon and 150 ml of tetrahydrofuran is hydrogenated on a Parr apparatus (50 psi, ambient temperature). Catalyst and drying agent are removed by filtration and the filtrate is quickly transferred to a flask under a nitrogen atmosphere. To the flask are added 0.85 gram of potassium tert-butoxide, 19.7 grams (229 mmol) of methyl acrylate, and 50 ml of tetrahydrofuran. The reaction mixture is stirred at ambient temperature for three hours and at 55° C. for one hour. The reaction mixture is partitioned between ether (300 ml) and saturated sodium bicarbonate solution (150 ml). The ether layer is washed with water (2×500 ml), washed with saturated aqueous sodium chloride (200 ml), dried over anhydrous magnesium sulfate and concentrated to an oil. The oil is purified by flash chromatography (silica gel; 9:1 hexane:ethyl acetate) to afford 13.0 grams of the title compound as a colorless liquid.
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