Technology Process of (S)-4-hydroxy-6-[2-(4-hydroxy-phenyl)ethyl]-6-isopropyl-5,6-dihydro-pyran-2-one
There total 15 articles about (S)-4-hydroxy-6-[2-(4-hydroxy-phenyl)ethyl]-6-isopropyl-5,6-dihydro-pyran-2-one which
guide to synthetic route it.
The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
synthetic route:
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: 80 percent / Ba(OH)2 / ethanol / 20 °C
2.1: 95 percent / H2 / Raney Ni / tetrahydrofuran / 20 °C / 1292.87 Torr
3.1: i-Pr2NH; n-BuLi / tetrahydrofuran / -40 - -15 °C
4.1: LiOH / methanol; H2O / Heating
5.1: (S)-α-methylbenzylamine / ethyl acetate / Heating
5.2: 1N HCl
6.1: CDI / tetrahydrofuran / 4 h / 20 °C
6.2: tetrahydrofuran / 20 °C
7.1: 0.1N NaOH / tetrahydrofuran / 20 °C
8.1: H2 / 20 percent Pd/C
With
barium dihydroxide; lithium hydroxide; sodium hydroxide; n-butyllithium; (S)-1-phenyl-ethylamine; hydrogen; diisopropylamine; 1,1'-carbonyldiimidazole;
palladium on activated charcoal; nickel;
In
tetrahydrofuran; methanol; ethanol; water; ethyl acetate;
1.1: Condensation / 2.1: Hydrogenation / 3.1: Condensation / 4.1: Hydrolysis / 5.1: salt formation; chiral resolution / 5.2: chiral resolution / 6.1: Substitution / 6.2: Substitution / 7.1: Cyclization / 8.1: Hydrogenolysis;
DOI:10.1016/S0968-0896(99)00215-1
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: 80 percent / Ba(OH)2 / ethanol / 20 °C
2.1: 95 percent / H2 / Raney Ni / tetrahydrofuran / 20 °C / 1292.87 Torr
3.1: i-Pr2NH; n-BuLi / tetrahydrofuran / -40 - -15 °C
4.1: LiOH / methanol; H2O / Heating
5.1: (S)-α-methylbenzylamine / ethyl acetate / Heating
5.2: 1N HCl
6.1: CDI / tetrahydrofuran / 4 h / 20 °C
6.2: tetrahydrofuran / 20 °C
7.1: 0.1N NaOH / tetrahydrofuran / 20 °C
8.1: H2 / 20 percent Pd/C
With
barium dihydroxide; lithium hydroxide; sodium hydroxide; n-butyllithium; (S)-1-phenyl-ethylamine; hydrogen; diisopropylamine; 1,1'-carbonyldiimidazole;
palladium on activated charcoal; nickel;
In
tetrahydrofuran; methanol; ethanol; water; ethyl acetate;
1.1: Condensation / 2.1: Hydrogenation / 3.1: Condensation / 4.1: Hydrolysis / 5.1: salt formation; chiral resolution / 5.2: chiral resolution / 6.1: Substitution / 6.2: Substitution / 7.1: Cyclization / 8.1: Hydrogenolysis;
DOI:10.1016/S0968-0896(99)00215-1
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: K2CO3 / acetone / 18 h / Heating
2.1: 3N LiOH / tetrahydrofuran; methanol / 20 °C
3.1: SOCl2 / 5 h / Heating
4.1: 82 percent / pyridine / CH2Cl2 / 18 h / 20 °C
5.1: 72 percent / tetrahydrofuran / 16 h / 20 °C
6.1: i-Pr2NH; n-BuLi / tetrahydrofuran / -40 - -15 °C
7.1: LiOH / methanol; H2O / Heating
8.1: (S)-α-methylbenzylamine / ethyl acetate / Heating
8.2: 1N HCl
9.1: CDI / tetrahydrofuran / 4 h / 20 °C
9.2: tetrahydrofuran / 20 °C
10.1: 0.1N NaOH / tetrahydrofuran / 20 °C
11.1: H2 / 20 percent Pd/C
With
pyridine; lithium hydroxide; sodium hydroxide; n-butyllithium; thionyl chloride; (S)-1-phenyl-ethylamine; hydrogen; potassium carbonate; diisopropylamine; 1,1'-carbonyldiimidazole;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetone;
1.1: Esterification / 2.1: Hydrolysis / 3.1: Chlorination / 4.1: Substitution / 5.1: Grignard reaction / 6.1: Condensation / 7.1: Hydrolysis / 8.1: salt formation; chiral resolution / 8.2: chiral resolution / 9.1: Substitution / 9.2: Substitution / 10.1: Cyclization / 11.1: Hydrogenolysis;
DOI:10.1016/S0968-0896(99)00215-1
