反应详情

A mixture of methyl 5-[4-acetonylphenoxy]furan-2-carboxylate (1.04 g) and 2-hydroxy-2-(3-chlorophenyl)ethanamine (0.65 ) in dry benzene (100 ml) was heated under reflux, with azeotropic removal of water, for 1 hr. the solvent was evaporated and the residue dissolved in methanol (100 ml), cooled, and treated with sodium borohydride (0.4 g), in portions. The reaction mixture was stirred at ambient temperature for 2 hr. The solvent was evaporated and the residue partitioned between water and chloroform. The organic layer was dried (MgSO4) and evaporated to an oil which was purified by column chromatography on silica gel. Elution with 4% methanol:chloroform gave a colourless oil. An ethereal solution of the free base was treated with hydrogen chloride gas to give methyl 5-[4-[2-[(3-chloro-β-hydroxyphenethyl)amino]propyl]phenoxy]furan-2-carboxylate, hydrochloride as a 65:35 mixture of diastereoisomers, m.p. 148°-150° C. (ethylacetate-ether).

1. temperaturewas heated
2. customthe solvent was evaporated
3. dissolutionthe residue dissolved in methanol (100 ml)
4. temperaturecooled
5. additiontreated with sodium borohydride (0.4 g), in portions
6. customThe solvent was evaporated
7. customthe residue partitioned between water and chloroform
8. dry with materialThe organic layer was dried (MgSO4)
9. customevaporated to an oil which
10. customwas purified by column chromatography on silica gel
11. washElution with 4% methanol
12. customchloroform gave a colourless oil