Technology Process of [(1S,4R,5S,6R,7R)-7-Hydroxy-4,8,8-trimethyl-6-(toluene-4-sulfonyloxymethyl)-spiro[4.4]non-1-yl]-acetic acid methyl ester
There total 14 articles about [(1S,4R,5S,6R,7R)-7-Hydroxy-4,8,8-trimethyl-6-(toluene-4-sulfonyloxymethyl)-spiro[4.4]non-1-yl]-acetic acid methyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 9 steps
1: NEt3 / CH2Cl2 / 3 h / -78 deg C to r.t.
2: 85 percent / CaCO3 / 1,2-dichloro-benzene / 3 h / 130 °C
3: 96 percent / MCPBA / CH2Cl2 / 4 h / -78 deg C to r.t.
4: 70 percent / Al(i-OPr)3 / toluene / 120 h / 110 °C
5: 1.) SOCl2 / 1.) hexane, 0 deg C, 1 h, 2.) DMSO, 80 deg C, 6 h
7: Al(i-OPr)3 / toluene / 3 h / 110 °C
8: 28 percent / BH3-DMS / hexane / 72 h / Ambient temperature
9: pyridine / 48 h / 0 - 4 °C
With
pyridine; thionyl chloride; dimethylsulfide borane complex; aluminum isopropoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; calcium carbonate;
In
hexane; dichloromethane; 1,2-dichloro-benzene; toluene;
DOI:10.1016/S0040-4039(97)00475-9
- Guidance literature:
-
Multi-step reaction with 13 steps
1: DIBA-H / hexane / 3 h / -78 °C
2: (COCl)2 / dimethylformamide / 2.5 h / 0 °C
3: 70 percent / ZnCl2 / CH2Cl2 / 4 h / -50 - 0 °C
4: tetrahydrofuran / 1 h / -78 - -20 °C
5: NEt3 / CH2Cl2 / 3 h / -78 deg C to r.t.
6: 85 percent / CaCO3 / 1,2-dichloro-benzene / 3 h / 130 °C
7: 96 percent / MCPBA / CH2Cl2 / 4 h / -78 deg C to r.t.
8: 70 percent / Al(i-OPr)3 / toluene / 120 h / 110 °C
9: 1.) SOCl2 / 1.) hexane, 0 deg C, 1 h, 2.) DMSO, 80 deg C, 6 h
11: Al(i-OPr)3 / toluene / 3 h / 110 °C
12: 28 percent / BH3-DMS / hexane / 72 h / Ambient temperature
13: pyridine / 48 h / 0 - 4 °C
With
pyridine; thionyl chloride; oxalyl dichloride; dimethylsulfide borane complex; aluminum isopropoxide; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; calcium carbonate; zinc(II) chloride;
In
tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 1,2-dichloro-benzene; toluene;
DOI:10.1016/S0040-4039(97)00475-9
- Guidance literature:
-
Multi-step reaction with 10 steps
1: tetrahydrofuran / 1 h / -78 - -20 °C
2: NEt3 / CH2Cl2 / 3 h / -78 deg C to r.t.
3: 85 percent / CaCO3 / 1,2-dichloro-benzene / 3 h / 130 °C
4: 96 percent / MCPBA / CH2Cl2 / 4 h / -78 deg C to r.t.
5: 70 percent / Al(i-OPr)3 / toluene / 120 h / 110 °C
6: 1.) SOCl2 / 1.) hexane, 0 deg C, 1 h, 2.) DMSO, 80 deg C, 6 h
8: Al(i-OPr)3 / toluene / 3 h / 110 °C
9: 28 percent / BH3-DMS / hexane / 72 h / Ambient temperature
10: pyridine / 48 h / 0 - 4 °C
With
pyridine; thionyl chloride; dimethylsulfide borane complex; aluminum isopropoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; calcium carbonate;
In
tetrahydrofuran; hexane; dichloromethane; 1,2-dichloro-benzene; toluene;
DOI:10.1016/S0040-4039(97)00475-9
