Technology Process of (1R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-4-methyl-cyclohex-3-enecarboxylic acid methoxy-methyl-amide
There total 9 articles about (1R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-4-methyl-cyclohex-3-enecarboxylic acid methoxy-methyl-amide which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(1R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-4-methyl-cyclohex-3-enecarboxylic acid;
With
1,1'-carbonyldiimidazole;
In
dichloromethane;
at 23 ℃;
for 0.166667h;
N,O-dimethylhydroxylamine*hydrochloride;
In
dichloromethane;
at 23 ℃;
for 3h;
DOI:10.1021/ja046695b
- Guidance literature:
-
Multi-step reaction with 9 steps
1: Amberlyst H+ resin; benzene / dimethylformamide / Heating
2: triethylamine; DMAP / dimethylformamide / 23 °C
3: pyridinium dichromate; Celite; molecular sieves 4 Angstroem / acetonitrile / 45 °C
4: t-BuOK / tetrahydrofuran / 65 °C
5: 74 percent / molecular sieves 4 Angstroem / 5.5 h / 23 °C
6: 98 percent / triethylamine; DMAP / CH2Cl2 / 0.17 h / 23 °C
7: 89 percent / Pd(P(t-Bu)3)2; N-methylmorpholine N-oxide; triethylsilane / tetrahydrofuran / 3.5 h / 70 °C
8: 99 percent / H2 / Pd/C / methanol / 7 h / 0 °C / 760 Torr
9: 93 percent / 1,1'-carbonyldiimidazole / CH2Cl2 / 23 °C
With
triethylsilane; dmap; dipyridinium dichromate; bis(tri-t-butylphosphine)palladium(0); 4 A molecular sieve; Amberlyst H+ resin; Celite; potassium tert-butylate; hydrogen; 4-methylmorpholine N-oxide; triethylamine; 1,1'-carbonyldiimidazole; benzene;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
4: Wittig olefination;
DOI:10.1021/ja050586v
- Guidance literature:
-
Multi-step reaction with 8 steps
1: triethylamine; DMAP / dimethylformamide / 23 °C
2: pyridinium dichromate; Celite; molecular sieves 4 Angstroem / acetonitrile / 45 °C
3: t-BuOK / tetrahydrofuran / 65 °C
4: 74 percent / molecular sieves 4 Angstroem / 5.5 h / 23 °C
5: 98 percent / triethylamine; DMAP / CH2Cl2 / 0.17 h / 23 °C
6: 89 percent / Pd(P(t-Bu)3)2; N-methylmorpholine N-oxide; triethylsilane / tetrahydrofuran / 3.5 h / 70 °C
7: 99 percent / H2 / Pd/C / methanol / 7 h / 0 °C / 760 Torr
8: 93 percent / 1,1'-carbonyldiimidazole / CH2Cl2 / 23 °C
With
triethylsilane; dmap; dipyridinium dichromate; bis(tri-t-butylphosphine)palladium(0); 4 A molecular sieve; Celite; potassium tert-butylate; hydrogen; 4-methylmorpholine N-oxide; triethylamine; 1,1'-carbonyldiimidazole;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
3: Wittig olefination;
DOI:10.1021/ja050586v
