Technology Process of (1R,4E,3aR,7aR)-4-bromomethylene-7a-methyl-1-[(1S)-methyl-2-p-toluenesulfonyloxyethyl]perhydroindene
There total 1 articles about (1R,4E,3aR,7aR)-4-bromomethylene-7a-methyl-1-[(1S)-methyl-2-p-toluenesulfonyloxyethyl]perhydroindene which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(bromomethyl)triphenyl phosphonium bromide;
With
sodium hexamethyldisilazane;
In
tetrahydrofuran;
at 0 ℃;
for 1h;
(S)-2-[(1R,3aR,7aR)-octahydro-7a-methyl-4-oxo-4H-inden-1-yl]propyl 4-methylbenzenesulfonate;
In
tetrahydrofuran;
at 0 ℃;
for 2h;
DOI:10.1021/ol035922w
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: dimethylsulfoxide / 1.5 h / 70 °C
2.1: 692 mg / DIBAL-H / CH2Cl2; toluene / 1.5 h / 0 °C
3.1: CrCl3; LiAlH4 / tetrahydrofuran / 1 h / 20 °C
4.1: 93 percent / DIBAL-H / toluene / 0 - 20 °C
5.1: 91 percent / pyridine / CH2Cl2 / 16 h / 0 °C
6.1: 93 percent / tetrapropylammonium perruthenate; N-methylmorpholine N-oxide / CH2Cl2 / 4 h / 20 °C
7.1: DIBAL-H / toluene / 1.5 h / -78 °C
7.2: 40 percent / MnO2 / CH2Cl2 / 38 h / 20 °C
8.1: Et3N / Pd(PPh3)4 / toluene / 1.5 h / 110 °C
8.2: 48 percent / MeOH; (+)-10-camphorsulfonic acid / 1.5 h / 0 - 20 °C
With
pyridine; chromium chloride; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene;
DOI:10.1021/ol035922w
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: dimethylsulfoxide / 1.5 h / 70 °C
2.1: 692 mg / DIBAL-H / CH2Cl2; toluene / 1.5 h / 0 °C
3.1: CrCl3; LiAlH4 / tetrahydrofuran / 1 h / 20 °C
4.1: Et3N / Pd(PPh3)4 / toluene / 1.5 h / 110 °C
4.2: 48 percent / MeOH; (+)-10-camphorsulfonic acid / 1.5 h / 0 - 20 °C
With
chromium chloride; lithium aluminium tetrahydride; diisobutylaluminium hydride; triethylamine;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene;
DOI:10.1021/ol035922w
