Technology Process of (2R,3aR,4R,9bR)-1,5-di-(tert-butoxycarbonyl)-8-methoxycarbonyl-2-[(tertbutyldiphenylsilyloxy)methyl]-4-(3-hydroxypropyl)-2,3,3a,4-tetrahydro-9bH-pyrrolo[3,2-c]quinoline
There total 12 articles about (2R,3aR,4R,9bR)-1,5-di-(tert-butoxycarbonyl)-8-methoxycarbonyl-2-[(tertbutyldiphenylsilyloxy)methyl]-4-(3-hydroxypropyl)-2,3,3a,4-tetrahydro-9bH-pyrrolo[3,2-c]quinoline 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:
-
(2R,3aS,9bR)-1,5-di-(tert-butoxycarbonyl)-8-methoxycarbonyl-4-(tert-butyldimethylsilyloxy)-2-[(tert-butyldiphenylsilyloxy)methyl]-2,3,3a,4-tetrahydro-9bH-pyrrolo[3,2-c]quinoline; allyltributylstanane;
With
boron trifluoride diethyl etherate;
In
dichloromethane;
at -5 ℃;
for 1h;
With
9-borabicyclo[3.3.1]nonane dimer;
In
tetrahydrofuran;
at 0 ℃;
for 3h;
With
sodium hydroxide; dihydrogen peroxide;
In
tetrahydrofuran; methanol;
for 0.5h;
DOI:10.1039/b611121a
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: 14.8 g / pyridine / DMAP / CH2Cl2 / 15 h
2.1: DMAP / acetonitrile / 2 h / 20 °C
2.2: 99 percent / DEAEA / acetonitrile / 1.5 h
3.1: 99 percent / HCl / tetrahydrofuran / 2.5 h / 20 °C
4.1: 88 percent / molecular sieves 4 Angstroem; LiBF4 / benzene / 8 h / Heating
5.1: 9 percent / BF3*OEt2; molecular sieves 4 Angstroem / CH2Cl2 / -40 - 0 °C
6.1: 94 percent / NaHMDS / tetrahydrofuran / 1.5 h / 20 °C
7.1: BF3*OEt2 / CH2Cl2 / 1 h / -5 °C
7.2: 9-BBN / tetrahydrofuran / 3 h / 0 °C
7.3: 83 percent / aq. NaOH; H2O2 / tetrahydrofuran; methanol / 0.5 h
With
pyridine; hydrogenchloride; lithium tetrafluoroborate; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium hexamethyldisilazane;
dmap;
In
tetrahydrofuran; dichloromethane; acetonitrile; benzene;
7.1: Hosomi-Sakurai;
DOI:10.1039/b611121a
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: H2; K2CO3 / Pd-C / tetrahydrofuran / 18 h / 20 °C / 760 Torr
2.1: 14.8 g / pyridine / DMAP / CH2Cl2 / 15 h
3.1: DMAP / acetonitrile / 2 h / 20 °C
3.2: 99 percent / DEAEA / acetonitrile / 1.5 h
4.1: 99 percent / HCl / tetrahydrofuran / 2.5 h / 20 °C
5.1: 88 percent / molecular sieves 4 Angstroem; LiBF4 / benzene / 8 h / Heating
6.1: 9 percent / BF3*OEt2; molecular sieves 4 Angstroem / CH2Cl2 / -40 - 0 °C
7.1: 94 percent / NaHMDS / tetrahydrofuran / 1.5 h / 20 °C
8.1: BF3*OEt2 / CH2Cl2 / 1 h / -5 °C
8.2: 9-BBN / tetrahydrofuran / 3 h / 0 °C
8.3: 83 percent / aq. NaOH; H2O2 / tetrahydrofuran; methanol / 0.5 h
With
pyridine; hydrogenchloride; lithium tetrafluoroborate; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; sodium hexamethyldisilazane; potassium carbonate;
dmap; palladium on activated charcoal;
In
tetrahydrofuran; dichloromethane; acetonitrile; benzene;
8.1: Hosomi-Sakurai;
DOI:10.1039/b611121a
![(2R,3aS,9bR)-1,5-di-(tert-butoxycarbonyl)-8-methoxycarbonyl-4-(tert-butyldimethylsilyloxy)-2-[(tert-butyldiphenylsilyloxy)methyl]-2,3,3a,4-tetrahydro-9bH-pyrrolo[3,2-c]quinoline](/Databaselist/images/loading.webp)
