Technology Process of (3S,4R)-3-(Benzo[1,3]dioxol-5-yloxymethyl)-4-(4-fluoro-phenyl)-piperidine-1-carboxylic acid methyl ester
There total 10 articles about (3S,4R)-3-(Benzo[1,3]dioxol-5-yloxymethyl)-4-(4-fluoro-phenyl)-piperidine-1-carboxylic acid methyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: 89 percent / pyridine; DMAP / CH2Cl2 / 2 h / 25 °C
2.1: magnesium / tetrahydrofuran / 25 °C
2.2: CuCN / tetrahydrofuran / 0.67 h / -18 °C
2.3: tetrahydrofuran / 0.67 h / -50 - 0 °C
3.1: potassium fluoride; hydrogen peroxide / dimethylformamide; H2O / 18 h / 25 °C
4.1: hydrogen / [Ir(COD)(PCy3)Pyr]PF6 / CH2Cl2 / 20 h / 25 °C / 760 Torr
5.1: PPh3; DIAD / tetrahydrofuran / 2 h / 50 °C
With
pyridine; dmap; potassium fluoride; di-isopropyl azodicarboxylate; hydrogen; dihydrogen peroxide; magnesium; triphenylphosphine;
Crabtree's catalyst;
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
3.1: Tamao oxidation;
DOI:10.1016/j.tet.2006.05.092
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: 95 percent / borane dimethyl sulfide complex / (S)-2-methyl-CBS-oxazaborolidine catalyst / CH2Cl2; tetrahydrofuran; toluene / 2 h / -20 °C
2.1: 89 percent / pyridine; DMAP / CH2Cl2 / 2 h / 25 °C
3.1: magnesium / tetrahydrofuran / 25 °C
3.2: CuCN / tetrahydrofuran / 0.67 h / -18 °C
3.3: tetrahydrofuran / 0.67 h / -50 - 0 °C
4.1: potassium fluoride; hydrogen peroxide / dimethylformamide; H2O / 18 h / 25 °C
5.1: hydrogen / [Ir(COD)(PCy3)Pyr]PF6 / CH2Cl2 / 20 h / 25 °C / 760 Torr
6.1: PPh3; DIAD / tetrahydrofuran / 2 h / 50 °C
With
pyridine; dmap; potassium fluoride; di-isopropyl azodicarboxylate; dimethylsulfide borane complex; hydrogen; dihydrogen peroxide; magnesium; triphenylphosphine;
Crabtree's catalyst; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole;
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene;
4.1: Tamao oxidation;
DOI:10.1016/j.tet.2006.05.092
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: 86 percent / CH2Cl2 / 18 h / 25 °C
2.1: 95 percent / borane dimethyl sulfide complex / (S)-2-methyl-CBS-oxazaborolidine catalyst / CH2Cl2; tetrahydrofuran; toluene / 2 h / -20 °C
3.1: 89 percent / pyridine; DMAP / CH2Cl2 / 2 h / 25 °C
4.1: magnesium / tetrahydrofuran / 25 °C
4.2: CuCN / tetrahydrofuran / 0.67 h / -18 °C
4.3: tetrahydrofuran / 0.67 h / -50 - 0 °C
5.1: potassium fluoride; hydrogen peroxide / dimethylformamide; H2O / 18 h / 25 °C
6.1: hydrogen / [Ir(COD)(PCy3)Pyr]PF6 / CH2Cl2 / 20 h / 25 °C / 760 Torr
7.1: PPh3; DIAD / tetrahydrofuran / 2 h / 50 °C
With
pyridine; dmap; potassium fluoride; di-isopropyl azodicarboxylate; dimethylsulfide borane complex; hydrogen; dihydrogen peroxide; magnesium; triphenylphosphine;
Crabtree's catalyst; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole;
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene;
5.1: Tamao oxidation;
DOI:10.1016/j.tet.2006.05.092