Technology Process of 3,9-Epoxy-3H-azirino(2,3-c)(1)benzazocine-5,8-dimethanol, 1,1a,2,8,9,9a-hexahydro-7,9-dihydroxy-, alpha(8)-carbamate
There total 12 articles about 3,9-Epoxy-3H-azirino(2,3-c)(1)benzazocine-5,8-dimethanol, 1,1a,2,8,9,9a-hexahydro-7,9-dihydroxy-, alpha(8)-carbamate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
lithium borohydride;
In
tetrahydrofuran; methanol;
at 20 ℃;
DOI:10.1002/anie.200290015
- Guidance literature:
-
Multi-step reaction with 12 steps
1.1: 86 percent / i-Pr2NEt / CH2Cl2
2.1: tris(dimethylamino)sulfonium difluorotrimethylsilicate; H2O / dimethylformamide / 20 °C
3.1: Dess-Martin periodinane
4.1: LDA / dimethylformamide / -45 °C
4.2: dimethylformamide; tetrahydrofuran
5.1: 70 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene
6.1: 96 percent / 2,6-lutidine / CH2Cl2 / -78 - 0 °C
7.1: dimethyldioxirane; aq. K2CO3 / CH2Cl2 / 0 - 20 °C
8.1: 92 percent / TBAF / tetrahydrofuran / 0 °C
9.1: CH2Cl2 / 0 °C
10.1: MeOH; silica gel / 20 °C
11.1: 60 percent / TMSBr / CH2Cl2 / -45 °C
12.1: 78 percent / LiBH4 / tetrahydrofuran; methanol / 20 °C
With
2,6-dimethylpyridine; methanol; lithium borohydride; trimethylsilyl bromide; tetrabutyl ammonium fluoride; tris(dimethylamino)sulfonium trimethylsilyldifluoride; water; 3,3-dimethyldioxirane; silica gel; potassium carbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
3.1: Dess-Martin oxidation;
DOI:10.1002/anie.200290015
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: Dess-Martin periodinane
2.1: LDA / dimethylformamide / -45 °C
2.2: dimethylformamide; tetrahydrofuran
3.1: 70 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene
4.1: 96 percent / 2,6-lutidine / CH2Cl2 / -78 - 0 °C
5.1: dimethyldioxirane; aq. K2CO3 / CH2Cl2 / 0 - 20 °C
6.1: 92 percent / TBAF / tetrahydrofuran / 0 °C
7.1: CH2Cl2 / 0 °C
8.1: MeOH; silica gel / 20 °C
9.1: 60 percent / TMSBr / CH2Cl2 / -45 °C
10.1: 78 percent / LiBH4 / tetrahydrofuran; methanol / 20 °C
With
2,6-dimethylpyridine; methanol; lithium borohydride; trimethylsilyl bromide; tetrabutyl ammonium fluoride; 3,3-dimethyldioxirane; silica gel; potassium carbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
1.1: Dess-Martin oxidation;
DOI:10.1002/anie.200290015