Technology Process of (3aR,4R,11aR)-1-(hydroxymethyl)-2-methyl-4-phenyl-3,3a,4,11a-tetrahydrobenzo[4,5]isothiazolo[2,3-a]cyclopenta[e]pyridine 10,10-dioxide
There total 2 articles about (3aR,4R,11aR)-1-(hydroxymethyl)-2-methyl-4-phenyl-3,3a,4,11a-tetrahydrobenzo[4,5]isothiazolo[2,3-a]cyclopenta[e]pyridine 10,10-dioxide which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(E)-6-oxohept-2-enal; 3-styryl-1,2-benzoisothiazole-1,1-dioxide;
With
(2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; benzoic acid;
In
chloroform;
at 25 ℃;
for 24h;
With
2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; sodium acetate;
In
dichloromethane;
at 35 ℃;
for 2h;
With
sodium tris(acetoxy)borohydride;
In
dichloromethane;
at 20 ℃;
for 0.5h;
Overall yield = 40 %; stereoselective reaction;
DOI:10.1021/ol501814p
- Guidance literature:
-
Multi-step reaction with 2 steps
1.1: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / 1,2-dichloro-ethane / 16 h / 50 °C
2.1: (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; benzoic acid / chloroform / 24 h / 25 °C
2.2: 2 h / 35 °C
2.3: 0.5 h / 20 °C
With
(2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride; benzoic acid;
In
chloroform; 1,2-dichloro-ethane;
2.1: |Diels-Alder Cycloaddition;
DOI:10.1021/ol501814p
