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

Base Information

Chemical Name:(6R,7R,13S,15S)-1-(p-toluenesulfonyl)-tetradecahydro-6,13-methano-dipyrido<1,2-a;3',2'-e>azocin-12-one
CAS No.:220384-63-4
Molecular Formula:C₂₂H₂₈N₂O₃S
Molecular Weight:400.542
Hs Code.:

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

There total 15 articles about (6R,7R,13S,15S)-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:

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

: 220384-63-4
(6R,7R,13S,15S)-1-(p-toluenesulfonyl)-tetradecahydro-6,13-methano-dipyrido<1,2-a;3',2'-e>azocin-12-one

Guidance literature:: Multi-step reaction with 11 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

10: pyridine, DMAP / CH₂Cl₂ / 0.5 h / Ambient temperature

11: AIBN, tributyltin hydride / benzene / 1 h / Heating

With pyridine; 2,6-dimethylpyridine; chromium(VI) oxide; methanol; dmap; palladium diacetate; potassium fluoride; 2,2'-azobis(isobutyronitrile); sulfuric acid; dihydrogen peroxide; tri-n-butyl-tin hydride; 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; benzene;
DOI:10.1021/ja983013+

Reference yield:

: 98-59-9
p-toluenesulfonyl chloride

: 220384-63-4
(6R,7R,13S,15S)-1-(p-toluenesulfonyl)-tetradecahydro-6,13-methano-dipyrido<1,2-a;3',2'-e>azocin-12-one

Guidance literature:: Multi-step reaction with 12 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

11: pyridine, DMAP / CH₂Cl₂ / 0.5 h / Ambient temperature

12: AIBN, tributyltin hydride / benzene / 1 h / Heating

With pyridine; 2,6-dimethylpyridine; chromium(VI) oxide; methanol; dmap; palladium diacetate; potassium fluoride; 2,2'-azobis(isobutyronitrile); sulfuric acid; dihydrogen peroxide; tri-n-butyl-tin hydride; 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; benzene;
DOI:10.1021/ja983013+

Reference yield:

: 220384-55-4
1-(p-toluenesulfonyl)-piperidin-3-one

: 220384-63-4
(6R,7R,13S,15S)-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: 1.) LHMDS / 1.) THF, from -78 deg C to 0 deg C, 2.) THF, -78 deg C

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

3: 2,6-lutidine / CH₂Cl₂ / 0.17 h / Ambient temperature

4: MeOH / CH₂Cl₂ / 0.25 h / Ambient temperature

5: Et₃N / CH₂Cl₂ / 3 h

6: pyridine*HF / 2 h / Ambient temperature

7: 1,3,5-trimethyl-benzene / 3.5 h / 165 °C

8: 63 percent / KF, KHCO₃, 30 percent aq. H₂O₂ / tetrahydrofuran; methanol / 1.5 h / Heating

9: pyridine, DMAP / CH₂Cl₂ / 0.5 h / Ambient temperature

10: AIBN, tributyltin hydride / benzene / 1 h / Heating

With pyridine; 2,6-dimethylpyridine; methanol; dmap; palladium diacetate; potassium fluoride; 2,2'-azobis(isobutyronitrile); dihydrogen peroxide; tri-n-butyl-tin hydride; tetrabutylammonium trifluoromethylsulfonate; potassium carbonate; potassium hydrogencarbonate; pyridine hydrogenfluoride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1,3,5-trimethyl-benzene; benzene;
DOI:10.1021/ja983013+