反应详情

温度

110 °C

(S)-Toluenesulfonic acid 5-methoxy-2,3-dihydro-benzofuran-2-ylmethyl ester (2.30g, 6.88 mmol) and 4-(4-methyl-benzyl)-piperidin-4-ol (1.62 g, 7.9 mmol) and Na2CO3 (1.10 g, 10.3 mmol) were suspended in DMF and heated at 110° C. for 1 hr. After cooling to ambient temperature distilled H2O and EtOAc were added (100 ml) and the mixture shaken, the organic phase was then separated and the aqueous phase extracted with EtOAc (10 ml). The combined organic extracts were then washed with satd. NaCl solution (100 ml) and the organic phase dried with Na2SO4, filtered and evaporated to afford a yellow oil. This foam was chromatographed over SiO2 (Merck 230-400 mesh) with CH2Cl2, and then with CH2Cl2—MeOH (97:3) to afford (S)-1-(5-methoxy-2,3-dihydro-benzofuran-2-ylmethyl)-4-(4-methyl-benzyl)-piperidin-4-ol (2.20 g, 6.0 mmol, 87% yield) as a yellow oil MS: m/e=368.2 (M+H+) [α]=+45.8° (c=1.0, CHCl3).

1. temperatureAfter cooling to ambient temperature
2. distillationdistilled H2O and EtOAc
3. additionwere added (100 ml)
4. customthe organic phase was then separated
5. extractionthe aqueous phase extracted with EtOAc (10 ml)
6. washThe combined organic extracts were then washed with satd
7. dry with materialNaCl solution (100 ml) and the organic phase dried with Na2SO4
8. filtrationfiltered
9. customevaporated
10. customto afford a yellow oil
11. customThis foam was chromatographed over SiO2 (Merck 230-400 mesh) with CH2Cl2