Technology Process of Benzoic acid (2R,3S)-1-acetyl-2-(4-methoxy-phenoxymethyl)-1,2,3,6-tetrahydro-pyridin-3-yl ester
There total 12 articles about Benzoic acid (2R,3S)-1-acetyl-2-(4-methoxy-phenoxymethyl)-1,2,3,6-tetrahydro-pyridin-3-yl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
diisopropyl (E)-azodicarboxylate; triphenylphosphine;
In
tetrahydrofuran;
at 0 ℃;
for 2h;
DOI:10.1016/S0040-4039(03)00218-1
- Guidance literature:
-
Multi-step reaction with 12 steps
1: 70 percent / K2OsO4*2H2O; (DHQD)2PHAL; LiOH / 2-methyl-propan-2-ol; H2O / 8 h / 4 °C
2: 80 percent / NaH / dimethylformamide / 8 h / 0 °C
3: 100 percent / LiBH4 / diethyl ether / 0.25 h
4: 100 percent / TEA; DMAP / CH2Cl2 / 4 h / 25 °C
5: 95 percent / KH; 18-crown-ether / tetrahydrofuran / 5 h / 25 °C
6: 100 percent / tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 25 °C
7: 90 percent / periodinane / CH2Cl2 / 1 h / 25 °C
8: 94 percent / LiBr; DBU / tetrahydrofuran / 2 h / 25 °C
9: 80 percent / Grubb's bis(tricyclohexylphosphinebenzylidene Ru(IV)Cl2 / toluene / 2 h / 90 °C
10: 85 percent / trifluoroacetic acid / CH2Cl2 / 0.5 h / 25 °C
11: 80 percent / DIPAD; Ph3P / tetrahydrofuran / 2 h / 0 °C
With
dmap; lithium hydroxide; potassium osmate(VI); lithium borohydride; 18-crown-ether; TEA; tetrabutyl ammonium fluoride; potassium hydride; sodium hydride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropyl (E)-azodicarboxylate; 1,4-bis(9-O-dihydroquinidine)phthalazine; triphenylphosphine; trifluoroacetic acid; lithium bromide;
Grubbs catalyst first generation;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
2: Sharpless asymmetric aminohydroxylation / 8: Dess-Martin oxidation / 9: Horner-Wadsworth-Emmons olefination / 10: ring closing metathesis / 12: Mitsunobu reaction;
DOI:10.1016/S0040-4039(03)00218-1
- Guidance literature:
-
Multi-step reaction with 11 steps
1: 70 percent / K2OsO4*2H2O; (DHQD)2PHAL; LiOH / 2-methyl-propan-2-ol; H2O / 8 h / 4 °C
2: 80 percent / NaH / dimethylformamide / 8 h / 0 °C
3: 100 percent / LiBH4 / diethyl ether / 0.25 h
4: 100 percent / TEA; DMAP / CH2Cl2 / 4 h / 25 °C
5: 95 percent / KH; 18-crown-ether / tetrahydrofuran / 5 h / 25 °C
6: 100 percent / tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 25 °C
7: 90 percent / periodinane / CH2Cl2 / 1 h / 25 °C
8: 94 percent / LiBr; DBU / tetrahydrofuran / 2 h / 25 °C
9: 80 percent / Grubb's bis(tricyclohexylphosphinebenzylidene Ru(IV)Cl2 / toluene / 2 h / 90 °C
10: 85 percent / trifluoroacetic acid / CH2Cl2 / 0.5 h / 25 °C
11: 80 percent / DIPAD; Ph3P / tetrahydrofuran / 2 h / 0 °C
With
dmap; lithium hydroxide; potassium osmate(VI); lithium borohydride; 18-crown-ether; TEA; tetrabutyl ammonium fluoride; potassium hydride; sodium hydride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropyl (E)-azodicarboxylate; 1,4-bis(9-O-dihydroquinidine)phthalazine; triphenylphosphine; trifluoroacetic acid; lithium bromide;
Grubbs catalyst first generation;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
1: Sharpless asymmetric aminohydroxylation / 7: Dess-Martin oxidation / 8: Horner-Wadsworth-Emmons olefination / 9: ring closing metathesis / 11: Mitsunobu reaction;
DOI:10.1016/S0040-4039(03)00218-1
