Technology Process of (2S,5S,6S,7S,8R,10aS)-octahydro-5-[(4-methoxyphenyl)methyl]-2-methylamino-1H-7,10a-methanopyrrolo[1,2-a]azocine-6,8-diol
There total 39 articles about (2S,5S,6S,7S,8R,10aS)-octahydro-5-[(4-methoxyphenyl)methyl]-2-methylamino-1H-7,10a-methanopyrrolo[1,2-a]azocine-6,8-diol 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
lithium aluminium tetrahydride;
In
tetrahydrofuran;
at 60 ℃;
for 16h;
DOI:10.1021/jo302362b
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: DMAP / CH2Cl2 / 12 h / 25 °C
2.1: NaN3 / dimethylformamide / 12 h / 25 °C
3.1: 90 percent / H2 / 5 percent Pd/C / ethanol / 760 Torr
4.1: 92 percent / NaH / dimethylformamide / 2 h / 25 °C
5.1: LiBH4 / diethyl ether / 2 h
6.1: aq. HCl / acetic acid / 12 h
7.1: 95 percent / Et3N / CH2Cl2 / 3 h / 25 °C
8.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 25 °C
9.1: KO-t-Bu / 2-methyl-propan-2-ol / 0.5 h / 25 °C
9.2: TFA / CH2Cl2 / 2 h / 25 °C
9.3: LAH / tetrahydrofuran / 2 h / Heating
With
hydrogenchloride; dmap; lithium borohydride; sodium azide; potassium tert-butylate; hydrogen; sodium hydride; Dess-Martin periodane; triethylamine;
palladium on activated charcoal;
In
diethyl ether; ethanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; tert-butyl alcohol;
1.1: Tosylation / 2.1: Substitution / 3.1: Hydrogenolysis / 4.1: Methylation / 5.1: Reduction / 6.1: Hydrolysis / 7.1: Acylation / 8.1: Oxidation / 9.1: Cyclization / 9.2: Hydrolysis / 9.3: Reduction;
DOI:10.1021/ja991160h
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: 90 percent / H2 / 5 percent Pd/C / ethanol / 760 Torr
2.1: 92 percent / NaH / dimethylformamide / 2 h / 25 °C
3.1: LiBH4 / diethyl ether / 2 h
4.1: aq. HCl / acetic acid / 12 h
5.1: 95 percent / Et3N / CH2Cl2 / 3 h / 25 °C
6.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 25 °C
7.1: KO-t-Bu / 2-methyl-propan-2-ol / 0.5 h / 25 °C
7.2: TFA / CH2Cl2 / 2 h / 25 °C
7.3: LAH / tetrahydrofuran / 2 h / Heating
With
hydrogenchloride; lithium borohydride; potassium tert-butylate; hydrogen; sodium hydride; Dess-Martin periodane; triethylamine;
palladium on activated charcoal;
In
diethyl ether; ethanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; tert-butyl alcohol;
1.1: Hydrogenolysis / 2.1: Methylation / 3.1: Reduction / 4.1: Hydrolysis / 5.1: Acylation / 6.1: Oxidation / 7.1: Cyclization / 7.2: Hydrolysis / 7.3: Reduction;
DOI:10.1021/ja991160h
