反应详情

温度

-20 °C

A solution of 3-cyclohexyl-1-[4-[4-(2-hydroxyphenyl)-1-piperidinyl]butan-1-yl]-2-imidazolidinone (1 g, prepared from 4-(2-hydroxyphenyl)piperidine (described in Example 5) and 1a by the method described in Example 4) in dry methylene chloride (10 ml) was cooled to −20° C. Isobutylene (5 ml, condensed at −25° C.) was added under a nitrogen atmosphere followed by addition of trifluoromethanesulfonic acid (0.4 ml). The mixture was stirred for 3 h at −20° C. followed by addition of triethylamine (2 mL). After warming to room temperature the reaction mixture was concentrated in vacuo followed by addition of 2 M ammonia and extraction with methylene chloride. The organic phase was dried over magnesium sulfate and concentrated in vacuo leaving an oil which was purified by flash chromatography (silica gel, eluent: ethyl acetate/MeOH/triethylamine 97:2:1). The resulting colorless oil was dissolved in a mixture of ethyl acetate and acetone. Addition of oxalic acid gave the title compound, 10a, as a crystalline material. Yield: 0.8 g, mp: 147-53° C. 1H NMR (DMSO-d6): δ 0.95-2.10 (m, 18H), 1.35 (s, 9H), 2.85-3.15 (m, 7H), 3.25 (s, 4H), 3.35-3.60 (m, 3H), 6.90-7.25 (m, 4H).

1. temperatureAfter warming to room temperature the reaction mixture
2. concentrationwas concentrated in vacuo
3. additionfollowed by addition of 2 M ammonia and extraction with methylene chloride
4. dry with materialThe organic phase was dried over magnesium sulfate
5. concentrationconcentrated in vacuo
6. customleaving an oil which
7. customwas purified by flash chromatography (silica gel, eluent: ethyl acetate/MeOH/triethylamine 97:2:1)
8. dissolutionThe resulting colorless oil was dissolved in a mixture of ethyl acetate and acetone
9. additionAddition of oxalic acid