(6R,7R,13R,14R,15S)-14-hydroxy-1-(p-toluenesulfonyl)-tetradecahydro-6,13-methano-dipyrido<1,2-a;3',2'-e>azocin-12-one

Base Information

Chemical Name:(6R,7R,13R,14R,15S)-14-hydroxy-1-(p-toluenesulfonyl)-tetradecahydro-6,13-methano-dipyrido<1,2-a;3',2'-e>azocin-12-one
CAS No.:220384-61-2
Molecular Formula:C₂₂H₂₈N₂O₄S
Molecular Weight:416.541
Hs Code.:

Synonyms:(6R,7R,13R,14R,15S)-14-hydroxy-1-(p-toluenesulfonyl)-tetradecahydro-6,13-methano-dipyrido<1,2-a;3',2'-e>azocin-12-one

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Chemical Property of (6R,7R,13R,14R,15S)-14-hydroxy-1-(p-toluenesulfonyl)-tetradecahydro-6,13-methano-dipyrido<1,2-a;3',2'-e>azocin-12-one

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Technology Process of (6R,7R,13R,14R,15S)-14-hydroxy-1-(p-toluenesulfonyl)-tetradecahydro-6,13-methano-dipyrido<1,2-a;3',2'-e>azocin-12-one

There total 13 articles about (6R,7R,13R,14R,15S)-14-hydroxy-1-(p-toluenesulfonyl)-tetradecahydro-6,13-methano-dipyrido<1,2-a;3',2'-e>azocin-12-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:

Reference yield: 63.0%

: 14-(fluoro-dimethyl-silanyl)-1-(toluene-4-sulfonyl)-1,2,3,4,6,6a,7,8,9,10,13,13a-dodecahydro-6,13-methano-dipyrido[1,2-a;3',2'-e]azocin-12-one

: (6S,7R,13S,14S,15R)-14-hydroxy-1-(p-toluenesulfonyl)-tetradecahydro-6,13-methano-dipyrido<1,2-a;3',2'-e>azocin-12-one

: 220384-61-2
(6R,7R,13R,14R,15S)-14-hydroxy-1-(p-toluenesulfonyl)-tetradecahydro-6,13-methano-dipyrido<1,2-a;3',2'-e>azocin-12-one

Guidance literature:: With potassium fluoride; dihydrogen peroxide; potassium hydrogencarbonate; In tetrahydrofuran; methanol; for 1.5h; Heating;
DOI:10.1021/ja983013+

Reference yield:

: 220384-68-9
1-(p-toluenesulfonyl)-piperidin-3-ol

: 220384-61-2
(6R,7R,13R,14R,15S)-14-hydroxy-1-(p-toluenesulfonyl)-tetradecahydro-6,13-methano-dipyrido<1,2-a;3',2'-e>azocin-12-one

Guidance literature:: Multi-step reaction with 9 steps

1: aq. CrO₃, H₂SO₄ / acetone / 2 h / Ambient temperature

2: 1.) LHMDS / 1.) THF, from -78 deg C to 0 deg C, 2.) THF, -78 deg C

3: 83 percent / n-Bu₄NOTf, aq. K₂CO₃, 14 percent Pd(OAc)2 / dimethylformamide / 14 h / 55 °C

4: 2,6-lutidine / CH₂Cl₂ / 0.17 h / Ambient temperature

5: MeOH / CH₂Cl₂ / 0.25 h / Ambient temperature

6: Et₃N / CH₂Cl₂ / 3 h

7: pyridine*HF / 2 h / Ambient temperature

8: 1,3,5-trimethyl-benzene / 3.5 h / 165 °C

9: 63 percent / KF, KHCO₃, 30 percent aq. H₂O₂ / tetrahydrofuran; methanol / 1.5 h / Heating

With 2,6-dimethylpyridine; chromium(VI) oxide; methanol; palladium diacetate; potassium fluoride; sulfuric acid; dihydrogen peroxide; tetrabutylammonium trifluoromethylsulfonate; potassium carbonate; potassium hydrogencarbonate; pyridine hydrogenfluoride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; 1,3,5-trimethyl-benzene;
DOI:10.1021/ja983013+

Reference yield:

: 98-59-9
p-toluenesulfonyl chloride

: 220384-61-2
(6R,7R,13R,14R,15S)-14-hydroxy-1-(p-toluenesulfonyl)-tetradecahydro-6,13-methano-dipyrido<1,2-a;3',2'-e>azocin-12-one

Guidance literature:: Multi-step reaction with 10 steps

1: Et₃N / CH₂Cl₂ / 3 h / Ambient temperature

2: aq. CrO₃, H₂SO₄ / acetone / 2 h / Ambient temperature

3: 1.) LHMDS / 1.) THF, from -78 deg C to 0 deg C, 2.) THF, -78 deg C

4: 83 percent / n-Bu₄NOTf, aq. K₂CO₃, 14 percent Pd(OAc)2 / dimethylformamide / 14 h / 55 °C

5: 2,6-lutidine / CH₂Cl₂ / 0.17 h / Ambient temperature

6: MeOH / CH₂Cl₂ / 0.25 h / Ambient temperature

7: Et₃N / CH₂Cl₂ / 3 h

8: pyridine*HF / 2 h / Ambient temperature

9: 1,3,5-trimethyl-benzene / 3.5 h / 165 °C

10: 63 percent / KF, KHCO₃, 30 percent aq. H₂O₂ / tetrahydrofuran; methanol / 1.5 h / Heating

With 2,6-dimethylpyridine; chromium(VI) oxide; methanol; palladium diacetate; potassium fluoride; sulfuric acid; dihydrogen peroxide; tetrabutylammonium trifluoromethylsulfonate; potassium carbonate; potassium hydrogencarbonate; pyridine hydrogenfluoride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; 1,3,5-trimethyl-benzene;
DOI:10.1021/ja983013+