Technology Process of 1-(2'-bromo-4'-methoxy-5'-hydroxybenzyl)-2-formyl-6-ketal-1,3,4,5,7,8-hexahydroisoquinoline
There total 7 articles about 1-(2'-bromo-4'-methoxy-5'-hydroxybenzyl)-2-formyl-6-ketal-1,3,4,5,7,8-hexahydroisoquinoline which
guide to synthetic route it.
The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
synthetic route:
- Guidance literature:
-
With
N-bromoacetamide;
In
tetrahydrofuran;
at 0 - 5 ℃;
for 0.5h;
DOI:10.1021/jo01303a045
- Guidance literature:
-
With
1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione;
In
chloroform; 1-Propyl acetate;
at -25 - -15 ℃;
for 1h;
Product distribution / selectivity;
- Guidance literature:
-
Multi-step reaction with 6 steps
1: 95 percent / 2 h / 200 °C
2: 2)Na(CN)BH3 / 1) cyclization, neutralization to pH 4-5 with concentrated aqueous NH3 2) reduction with Na(CN)BH3 in refluxing 65percent MeOH for 1.5h
3: 90 percent / Li, NH3 (liquid) / tetrahydrofuran; 2-methyl-propan-2-ol / 1) 4h -55 to -65 deg C 2) 1.5h -75 deg C
4: 94 percent / ethyl acetate / Heating
5: 100 percent / CH3SO3H / tetrahydrofuran / 1 h / 25 °C
6: 88 percent / N-bromoacetamide (NBA) / tetrahydrofuran / 0.5 h / 0 - 5 °C
With
ammonia; lithium; sodium cyanoborohydride; N-bromoacetamide;
methanesulfonic acid;
In
tetrahydrofuran; ethyl acetate; tert-butyl alcohol;
DOI:10.1021/jo01303a045
