反应详情

A solution of crude (R)-5-(1-Phenyl-ethylamino)-3,6-dihydro-2H-pyran-4-carboxylic acid ethyl ester (4.53 g, ca. 16.5 mmol) was dissolved in trifluoroacetic acid (45 mL) and treated with triethylsilane (7.9 mL, 49.4 mmol). The mixture was stirred for 17 h and then concentrated. The residue was dissolved in water and adjusted to pH 10 with 50% sodium hydroxide. The mixture was extracted with dichloromethane, and the combined organic phases were dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography (40% diethyl ether/petroleum ether) to provide the product as a colorless oil (1.63 g, 36%). 1H NMR (300 mHz, CDCl3) δ7.22 (m, 4H), 7.16 (m, 1H), 4.14 (q, J=7.3 Hz, 2H), 3.77 (m, 2H), 3.60 (q, J=7.3 Hz, 1H), 3.23 (m, 1H), 2.83 (m, 2H), 2.31 (m, 1H), 1.77 (m, 2H), 1.24 (m, 6H), ESI MS: (M+H)+=278.1 (100%).

1. concentrationconcentrated
2. dissolutionThe residue was dissolved in water
3. extractionThe mixture was extracted with dichloromethane
4. dry with materialthe combined organic phases were dried (Na2SO4)
5. concentrationconcentrated
6. customThe residue was purified by flash column chromatography (40% diethyl ether/petroleum ether)