반응 #93583
ord-441a4a04acb14102806f129ee8725680
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후처리
- 1workup.ADDITIONwas added to a flask
- 2기타evacuated
- 3기타to remove oxygen
- 4workup.ADDITIONThe catalyst, 5% Pd in carbon (50% water, 19 g, Engelhard Co.), was added under an N2 atmosphere
- 5workup.ADDITIONsolid HCO2NH4 (65 g, Aldrich) was added
- 6workup.STIRRINGthe resulting mixture stirred for 1 hour
- 7온도The mixture was then slowly heated to 50° C. for 48 hours
- 8온도cooled to room temperature
- 9여과filtered through Celite (50 g)
- 10세척The solids were washed with methanol (50 mL)
- 11농축the filtrates concentrated in vacuo
- 12workup.DISSOLUTIONthe resulting solid dissolved in CH2Cl2
- 13추출The solution was extracted with saturated aqueous NH4Cl (500 mL) and saturated aqueous NaHCO3 (300 mL)
- 14기타the organic layer evaporated
실험 절차
A mixture of 1-(3,4-dimethoxyphenyl)-2-nitro-6-cyano-6-(i-propyl)-6-(3,4-dimethoxyphenyl)hexane (10, 58.7 g, 0.125 mol) and methanol (950 mL) was added to a flask, and evacuated to remove oxygen. The catalyst, 5% Pd in carbon (50% water, 19 g, Engelhard Co.), was added under an N2 atmosphere. After stirring for 10 minutes at room temperature, solid HCO2NH4 (65 g, Aldrich) was added, and the resulting mixture stirred for 1 hour. The mixture was then slowly heated to 50° C. for 48 hours, then cooled to room temperature and filtered through Celite (50 g). The solids were washed with methanol (50 mL), the filtrates concentrated in vacuo, and the resulting solid dissolved in CH2Cl2. The solution was extracted with saturated aqueous NH4Cl (500 mL) and saturated aqueous NaHCO3 (300 mL), and the organic layer evaporated to yield 1-(3,4-dimethoxyphenyl)-2-amino-6-cyano- 6-(i-propyl)-6-(3,4-dimethoxyphenyl)hexane (11, 52.3 g, MS m/e 440(M+)) as a pale yellow oil.