反应详情

A solution of N-(4-acetoxyphenylacetyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline (33.0 g, 0.086 m) in 50 ml of tetrahydrofuran was added dropwise to a stirred suspension of lithium aluminum hydride (8.8 g, 0.233 m) in 500 ml dry tetrahydrofuran maintained under nitrogen. The mixture was stirred at ambient temperature for 24 hours, then cooled with an ice bath and carefully treated with 24 ml of a saturated ammonium chloride solution. The salts were removed by filtration, the filtrate dried over MgSO4 and evaporated on an aspirator to a pale yellow oil, 23.2 g (77% yield). The hydrochloride salt was prepared in 100 ml of 1:1 isopropanol:methanol and recrystallization and vacuum drying of the white solid gave 14.7 g of N-(4-hydroxyphenethyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline hydrochloride, m.p. 225°-226°.

1. temperaturemaintained under nitrogen
2. temperaturecooled with an ice bath
3. customThe salts were removed by filtration
4. dry with materialthe filtrate dried over MgSO4
5. customevaporated on an aspirator to a pale yellow oil, 23.2 g (77% yield)
6. custommethanol and recrystallization and vacuum
7. customdrying of the white solid