反应详情

[2-(benzyloxy)ethoxy]acetaldehyde was prepared by Swern oxidation of commercially available 2-[2-(benzyloxy)ethoxy]ethanol. A 0.15M solution of the foregoing aldehyde and methyl (7R)-7-amino-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (prepared as described in Example 1, Step 4) in CH(OMe)3 was stirred overnight at RT; the residue obtained after removing volatiles in vacuo was dissolved in MeOH (0.15M solution), NaCNBH3 (2.3 eq) was added and the mixture was left stirring for 4 h. All volatiles were evaporated and the residual material was dissolved in EtOAc and washed with sat. aq. NaHCO3 and brine. After drying over Na2SO4 all volatiles were evaporated in vacuo; FC (Biotage, PE/EtOAc 1:1 to 1:3 with 0.5% NEt3) afforded 35% of methyl (7R)-7-({2-[2-(benzyloxy)ethoxy]ethyl}amino)-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate.

1. customthe residue obtained
2. customafter removing volatiles in vacuo
3. dissolutionwas dissolved in MeOH (0.15M solution)
4. waitthe mixture was left
5. customAll volatiles were evaporated
6. dissolutionthe residual material was dissolved in EtOAc
7. washwashed with sat. aq. NaHCO3 and brine
8. dry with materialAfter drying over Na2SO4 all volatiles
9. customwere evaporated in vacuo