Technology Process of (1aS,9aS)-3-[(4,5-dimethoxy-2-nitrophenyl)methyl] 1-methyl ester 5-methanol-1a,2,3,8,9,9a-hexahydro-7-(methoxymethoxy)-9-hydroxy-1H-aziridino[2,3-c][1]benzazocine-1,3(2H)-dicarboxylic acid
There total 11 articles about (1aS,9aS)-3-[(4,5-dimethoxy-2-nitrophenyl)methyl] 1-methyl ester 5-methanol-1a,2,3,8,9,9a-hexahydro-7-(methoxymethoxy)-9-hydroxy-1H-aziridino[2,3-c][1]benzazocine-1,3(2H)-dicarboxylic acid which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 11 steps
1: 90 percent / NaOMe / methanol; dimethylformamide / 3.5 h
2: 96 percent / imidazole / dimethylformamide / 24 h
3: 93 percent / DDQ; H2O / CH2Cl2 / 1.5 h
4: 82 percent / Dess-Martin reagent / CH2Cl2 / 2.5 h
5: H2 / Pd/C / methanol / 0.13 h
6: MgSO4; 4A molecular sieves / CH2Cl2 / Heating
7: 110 mg / NaCNBH3; TFA / CH2Cl2; H2O / 0.07 h
8: 88 percent / iPr2NEt; DMAP / CH2Cl2 / 4 h
9: 61 percent / DIBAL / CH2Cl2; hexane / 5 h / -78 °C
10: 85 percent / TBAF / tetrahydrofuran / 4 h / 20 °C
11: 14 mg / pyridine / 2.5 h
With
pyridine; 1H-imidazole; dmap; 4 A molecular sieve; tetrabutyl ammonium fluoride; water; hydrogen; sodium methylate; diisobutylaluminium hydride; sodium cyanoborohydride; magnesium sulfate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide;
1: Addition / 2: Substitution / 3: Substitution / 4: Oxidation / 5: Catalytic hydrogenation / 6: Cyclization / 7: Reduction / 8: Acylation / 9: Reduction / 10: Substitution / 11: Carboxylation;
DOI:10.1016/S0040-4020(99)01046-7
- Guidance literature:
-
Multi-step reaction with 7 steps
1: H2 / Pd/C / methanol / 0.13 h
2: MgSO4; 4A molecular sieves / CH2Cl2 / Heating
3: 110 mg / NaCNBH3; TFA / CH2Cl2; H2O / 0.07 h
4: 88 percent / iPr2NEt; DMAP / CH2Cl2 / 4 h
5: 61 percent / DIBAL / CH2Cl2; hexane / 5 h / -78 °C
6: 85 percent / TBAF / tetrahydrofuran / 4 h / 20 °C
7: 14 mg / pyridine / 2.5 h
With
pyridine; dmap; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; sodium cyanoborohydride; magnesium sulfate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water;
1: Catalytic hydrogenation / 2: Cyclization / 3: Reduction / 4: Acylation / 5: Reduction / 6: Substitution / 7: Carboxylation;
DOI:10.1016/S0040-4020(99)01046-7
- Guidance literature:
-
Multi-step reaction with 10 steps
1: 96 percent / imidazole / dimethylformamide / 24 h
2: 93 percent / DDQ; H2O / CH2Cl2 / 1.5 h
3: 82 percent / Dess-Martin reagent / CH2Cl2 / 2.5 h
4: H2 / Pd/C / methanol / 0.13 h
5: MgSO4; 4A molecular sieves / CH2Cl2 / Heating
6: 110 mg / NaCNBH3; TFA / CH2Cl2; H2O / 0.07 h
7: 88 percent / iPr2NEt; DMAP / CH2Cl2 / 4 h
8: 61 percent / DIBAL / CH2Cl2; hexane / 5 h / -78 °C
9: 85 percent / TBAF / tetrahydrofuran / 4 h / 20 °C
10: 14 mg / pyridine / 2.5 h
With
pyridine; 1H-imidazole; dmap; 4 A molecular sieve; tetrabutyl ammonium fluoride; water; hydrogen; diisobutylaluminium hydride; sodium cyanoborohydride; magnesium sulfate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide;
1: Substitution / 2: Substitution / 3: Oxidation / 4: Catalytic hydrogenation / 5: Cyclization / 6: Reduction / 7: Acylation / 8: Reduction / 9: Substitution / 10: Carboxylation;
DOI:10.1016/S0040-4020(99)01046-7
