Technology Process of (3aR,10aS,10bR)-octahydro-2H-furo[3,2-c]pyrrolo[1,2-a]azepine-2,8(1H)-dione
There total 1 articles about (3aR,10aS,10bR)-octahydro-2H-furo[3,2-c]pyrrolo[1,2-a]azepine-2,8(1H)-dione 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:
-
Multi-step reaction with 13 steps
1.1: 80 percent / NaH
2.1: 95 percent / TBAF
3.1: CuBr*DMS; LiBr / tetrahydrofuran / 0.5 h / -78 °C
3.2: 81 percent / tetrahydrofuran / 1 h / -78 - -40 °C
4.1: 95 percent / Grubbs II catalyst / CH2Cl2 / Heating
5.1: 83 percent / NaOH / methanol
6.1: 91 percent / aq. NaHCO3; I2
7.1: 70 percent / Bu3SnH; AIBN / toluene / 10 h / Heating
8.1: 81 percent / LiHMDS
9.1: 76 percent / H2O2
10.1: 78 percent / NiCl2; NaBH4
With
sodium hydroxide; sodium tetrahydroborate; copper(I) bromide dimethylsulfide complex; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; dihydrogen peroxide; iodine; tri-n-butyl-tin hydride; sodium hydride; sodium hydrogencarbonate; lithium bromide; nickel dichloride; lithium hexamethyldisilazane;
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride;
In
tetrahydrofuran; methanol; dichloromethane; toluene;
4.1: Swern oxidation / 5.1: Wittig reaction;
DOI:10.1055/s-2004-822927
- Guidance literature:
-
(3aR,10aS,10bR)-octahydro-2H-furo[3,2-c]pyrrolo[1,2-a]azepine-2,8(1H)-dione;
With
lithium hexamethyldisilazane;
In
tetrahydrofuran;
at -78 - -40 ℃;
for 1h;
Inert atmosphere;
iodomethane;
In
tetrahydrofuran;
at -78 - 20 ℃;
for 2.25h;
diastereoselective reaction;
Inert atmosphere;
DOI:10.1021/jacs.7b10944
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 - -40 °C / Inert atmosphere
1.2: 2.25 h / -78 - 20 °C / Inert atmosphere
2.1: bis(triphenylphosphine)iridium(I) carbonyl chloride; 1,1,3,3-Tetramethyldisiloxane / toluene / 1 h / 20 °C / Inert atmosphere
3.1: ortho-nitrobenzoic acid / toluene; acetonitrile / 24 h / 20 °C / Inert atmosphere
4.1: hydrogen; Rh/alumina / ethanol / 3 h / 20 °C / 760.05 Torr
With
bis(triphenylphosphine)iridium(I) carbonyl chloride; 1,1,3,3-Tetramethyldisiloxane; ortho-nitrobenzoic acid; Rh/alumina; hydrogen; lithium hexamethyldisilazane;
In
tetrahydrofuran; ethanol; toluene; acetonitrile;
DOI:10.1021/jacs.7b10944
