반응 #527674
ord-dd7549bd12774a3cb0e3b4a84ddb0bb8
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후처리
- 1기타prepared in a similar manner to that
- 2기타the solvents removed by evaporation
- 3기타The residue was partitioned between ethyl acetate and dilute aqueous sodium hydroxide solution
- 4기타The organic layer yielded a gum which
- 5온도under reflux for 1 hour
- 6기타The solvents were removed by evaporation
- 7기타the residue partitioned between ether and saturated aqueous sodium bicarbonate solution
- 8기타The ether layer yielded a residue which
- 9기타The solvent was removed by evaporation
- 10기타the residue crystallised
- 11기타recrystallised from propan-2-ol
실험 절차
A mixture of the hydrochloride salt of 7-benzyloxy-1-[1-(2-chlorophenyl)cyclobutyl]-6-methoxy-1,2,3,4-tetrahydroisoquinoline (2.75 g prepared in a similar manner to that described in Example RB25), methanol (50 ml) and 37-40% aqueous formaldehyde solution (3 ml) was cooled to 10° C. and sodium cyanoborohydride (1.52 g) was added. The mixture was stirred for 24 hours and the solvents removed by evaporation. The residue was partitioned between ethyl acetate and dilute aqueous sodium hydroxide solution. The organic layer yielded a gum which was dissolved in methanol (25 ml) and concentrated hydrochloric acid (25 ml) and heated under reflux for 1 hour. The solvents were removed by evaporation and the residue partitioned between ether and saturated aqueous sodium bicarbonate solution. The ether layer yielded a residue which was dissolved in propan-2-ol (100 ml) and 48% aqueous hydrobromic acid (5 ml). The solvent was removed by evaporation and the residue crystallised and then recrystallised from propan-2-ol to give 1-[1-(2-chlorophenyl)cyclobutyl]-7-hydroxy-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline hydrobromide, m.p. 148°-150° C.