(6S,9R)-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-6,9-diol

Base Information

Chemical Name:(6S,9R)-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-6,9-diol
CAS No.:1289024-24-3
Molecular Formula:C₁₆H₁₅F₂NO₂
Molecular Weight:291.297
Hs Code.:

Synonyms:(6S,9R)-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-6,9-diol

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Chemical Property of (6S,9R)-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-6,9-diol

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Technology Process of (6S,9R)-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-6,9-diol

There total 14 articles about (6S,9R)-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-6,9-diol 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:

Reference yield: 86.0%

: 1289024-22-1
(6S,9R)-6-(2,3-difluorophenyl)-6-hydroxy-6,7,8,9-tetrahydro-5H-cyclohepta[b]-pyridin-9-yl 4-nitrobenzoate

: 1289024-24-3
(6S,9R)-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-6,9-diol

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 2h;

Reference yield:

: 1190363-43-9
5S⁽⁹⁾-hydroxy-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one

: 1289024-24-3
(6S,9R)-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-6,9-diol

Guidance literature:: Multi-step reaction with 10 steps

1.1: triethylamine / dichloromethane / 1 h / 0 °C

2.1: sodium tetrahydroborate; methanol / 1 h / 20 °C

3.1: Burgess Reagent / benzene / 5 h / Reflux; Inert atmosphere

4.1: sodium hypochlorite; disodium hydrogenphosphate / (-)-chloro((1R,2R)-4,4',6,6'-tetra-tert-butyl-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato)manganese(III) / dichloromethane / 21 h / 0 - 20 °C / Reflux

5.1: hydrogen / palladium 10% on activated carbon / methanol / 3 h / 20 °C / 760.05 Torr

6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.67 h / -55 - -50 °C

6.2: 0.5 h / -50 - -20 °C

7.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -65 - -60 °C / Inert atmosphere

7.2: 1.5 h / -78 - 20 °C

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 50 °C

9.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 15 h / Inert atmosphere

10.1: lithium hydroxide / tetrahydrofuran / 2 h / 20 °C

With methanol; sodium hypochlorite; sodium tetrahydroborate; disodium hydrogenphosphate; n-butyllithium; oxalyl dichloride; Burgess Reagent; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium hydroxide; (-)-chloro((1R,2R)-4,4',6,6'-tetra-tert-butyl-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato)manganese(III); palladium 10% on activated carbon; In tetrahydrofuran; methanol; hexane; dichloromethane; benzene; 6.1: Swern Oxidation / 6.2: Swern Oxidation / 9.1: Mitsunobu reaction;

Reference yield:

: 1289024-08-3
(1aS,4S,8bR)-4-((triisopropylsilyl)oxy)-1a,3,4,8b-tetrahydro-2Hoxireno[2′,3′:3,4]cyclohepta[1,2-b]pyridine

: 1289024-24-3
(6S,9R)-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-6,9-diol

Guidance literature:: Multi-step reaction with 6 steps

1.1: hydrogen / palladium 10% on activated carbon / methanol / 3 h / 20 °C / 760.05 Torr

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.67 h / -55 - -50 °C

2.2: 0.5 h / -50 - -20 °C

3.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -65 - -60 °C / Inert atmosphere

3.2: 1.5 h / -78 - 20 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 50 °C

5.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 15 h / Inert atmosphere

6.1: lithium hydroxide / tetrahydrofuran / 2 h / 20 °C

With n-butyllithium; oxalyl dichloride; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triphenylphosphine; lithium hydroxide; palladium 10% on activated carbon; In tetrahydrofuran; methanol; hexane; dichloromethane; 2.1: Swern Oxidation / 2.2: Swern Oxidation / 5.1: Mitsunobu reaction;