Technology Process of (R,S)-(1l,2u,5u,7x)-7-<<(tert-butyldimethylsilyl)oxy>methyl>bicyclo<3.3.1>nonan-2-ol
There total 1 articles about (R,S)-(1l,2u,5u,7x)-7-<<(tert-butyldimethylsilyl)oxy>methyl>bicyclo<3.3.1>nonan-2-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 7 steps
1: 83 percent / 1 M NaOH / dioxane / 16 h / 185 °C
2: 1.) BF3*THF, 2.) 10percent NaOH, 30percent aq. H2O2 / 1.) RT, 90 min, 2.) a) RT, 20 min, b) 50 deg C, 15 min
3: 80 percent / imidazole, DMAP / dimethylformamide / 1.) RT, 5 h, 2.) 45 deg C, overnight
4: 100 percent / triethylamine / CH2Cl2 / 1 h / 0 °C
5: 92 percent / t-BuOK / tetrahydrofuran / 2 h / Ambient temperature
6: 98 percent / m-chloroperoxybenzoic acid, NaHCO3 / CH2Cl2 / 1 h / Ambient temperature
7: 72 percent / lithium triethylborohydride / tetrahydrofuran / 4 h / 45 °C
With
1H-imidazole; dmap; sodium hydroxide; boron trifluoride-tetrahydrofuran complex; potassium tert-butylate; dihydrogen peroxide; lithium triethylborohydride; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00006a042
- Guidance literature:
-
Multi-step reaction with 5 steps
1: 1.) n-BuLi / 1.) Et2O, -5 deg C, 5 min, 2.) RT, 30 min
2: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 8 h / Ambient temperature
3: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) Et3N / 1.) -78 deg C, 30 min, 2.) from -78 deg C to RT, 35 min
4: 1.) t-BuOK / 1.) THF, 2-methyl-2-propanol, RT, 5 min, 2.) RT, 35 min
5: 1.) n-BuLi / 1.) THF, hexane, RT, 2.) RT, 20 min
With
n-butyllithium; oxalyl dichloride; potassium tert-butylate; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran;
DOI:10.1021/ja00006a042
- Guidance literature:
-
Multi-step reaction with 2 steps
1: 1.) n-BuLi / 1.) Et2O, -5 deg C, 5 min, 2.) RT, 30 min
2: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 8 h / Ambient temperature
With
n-butyllithium; tetrabutyl ammonium fluoride;
In
tetrahydrofuran;
DOI:10.1021/ja00006a042
