(2α,3aβ,6aα,9aα)-(+/-)-decahydro-2-methylpyrido<2,1,6-de>quinolizin-1(2H)-one tosylhydrazone

Base Information

Chemical Name:(2α,3aβ,6aα,9aα)-(+/-)-decahydro-2-methylpyrido<2,1,6-de>quinolizin-1(2H)-one tosylhydrazone
CAS No.:75509-49-8
Molecular Formula:C₂₀H₂₉N₃O₂S
Molecular Weight:375.535
Hs Code.:

Synonyms:(2α,3aβ,6aα,9aα)-(+/-)-decahydro-2-methylpyrido<2,1,6-de>quinolizin-1(2H)-one tosylhydrazone

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Chemical Property of (2α,3aβ,6aα,9aα)-(+/-)-decahydro-2-methylpyrido<2,1,6-de>quinolizin-1(2H)-one tosylhydrazone

Chemical Property:

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Technology Process of (2α,3aβ,6aα,9aα)-(+/-)-decahydro-2-methylpyrido<2,1,6-de>quinolizin-1(2H)-one tosylhydrazone

There total 28 articles about (2α,3aβ,6aα,9aα)-(+/-)-decahydro-2-methylpyrido<2,1,6-de>quinolizin-1(2H)-one tosylhydrazone 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: 72.0%

: 89959-66-0
(2α,3aβ,6aα,9aα)-(+/-)-decahydro-2-methylpyrido<2,1,6-de>quinolizin-1(2H)-one hydrazone

: 98-59-9
p-toluenesulfonyl chloride

: 75509-49-8
(2α,3aβ,6aα,9aα)-(+/-)-decahydro-2-methylpyrido<2,1,6-de>quinolizin-1(2H)-one tosylhydrazone

Guidance literature:: With triethylamine; In dichloromethane; 1) 0 deg C, 15 min, 2) 20 deg C, 3 h;
DOI:10.1021/jo00186a029

Reference yield:

: 57194-67-9
(3aα,6aα,9aβ)-dodecahydropyrido<2,1,6-de>quinolizine

: 75509-49-8
(2α,3aβ,6aα,9aα)-(+/-)-decahydro-2-methylpyrido<2,1,6-de>quinolizin-1(2H)-one tosylhydrazone

Guidance literature:: Multi-step reaction with 14 steps

1: 97 percent / H₂, HOAc / 10 percent Pd on carbon / propan-2-ol / 21 h / 190 °C

2: 83 percent / EDTA, Hg(OAc)2 / aq. NaOH; acetic acid / 4.5 h / Heating

3: 2.11 g / concentrated HCl / H₂O; diethyl ether / 17 h / 25 °C

4: 80 percent / fuming H₂SO₄ (30 percent SO₃) / 50 h / 50 °C

5: 71 percent / EDTA, Hg(OAc)2 / aq. NaOH; acetic acid / 4 h / Heating

6: 94 percent / H₂ / 10 percent Pt on C / methanol; acetic acid / 60 h / 3040 Torr

7: 200 mg / POCl₃ / pyridine; CHCl₃ / 7 h / Heating

8: 1) borane-dimethyl sulfide complex, 2) 30 percent H₂O₂ / 1) dry THF, 0-5 deg C, 8.5 h; room temperature, 12 h, 2) 2.5 N aqueous NaOH, room temperature, 1 h; reflux, 1.5 h

9: 76 percent / concentrated H₂SO₄, Jones reagent / acetic acid / 1 h / 20 °C

10: 87 percent / 10 h / 60 - 65 °C

11: 99 percent / lithium bronze reagent (from Li and liquid NH₃), t-butyl alcohol / tetrahydrofuran / 0.5 h / Ambient temperature

12: 74 percent / H₂ / 10 percent Pd on C / ethanol; acetic acid / 0.5 h / 760 Torr

13: 95 percent hydrazine / ethanol / 4 h / 20 °C

14: 72 percent / Et₃N / CH₂Cl₂ / 1) 0 deg C, 15 min, 2) 20 deg C, 3 h

With hydrogenchloride; jones reagent; ethylenediaminetetraacetic acid; dimethylsulfide borane complex; lithium bronze reagent (from Li and liquid NH₃); sulfuric acid; sulfur trioxide; mercury(II) diacetate; hydrogen; dihydrogen peroxide; hydrazine hydrate; acetic acid; triethylamine; tert-butyl alcohol; trichlorophosphate; palladium on activated charcoal; platinum on activated charcoal; In tetrahydrofuran; pyridine; methanol; sodium hydroxide; diethyl ether; ethanol; dichloromethane; chloroform; water; acetic acid; isopropyl alcohol;
DOI:10.1021/jo00186a029

Reference yield:

: 61714-12-3
(+/-)-trans-13-azabicyclo<7.3.1>tridecan-5-ol

: 75509-49-8
(2α,3aβ,6aα,9aα)-(+/-)-decahydro-2-methylpyrido<2,1,6-de>quinolizin-1(2H)-one tosylhydrazone

Guidance literature:: Multi-step reaction with 15 steps

1: 68 percent / p-toluenesulfonic acid / xylene / 3 h / Heating

2: 97 percent / H₂, HOAc / 10 percent Pd on carbon / propan-2-ol / 21 h / 190 °C

3: 83 percent / EDTA, Hg(OAc)2 / aq. NaOH; acetic acid / 4.5 h / Heating

4: 2.11 g / concentrated HCl / H₂O; diethyl ether / 17 h / 25 °C

5: 80 percent / fuming H₂SO₄ (30 percent SO₃) / 50 h / 50 °C

6: 71 percent / EDTA, Hg(OAc)2 / aq. NaOH; acetic acid / 4 h / Heating

7: 94 percent / H₂ / 10 percent Pt on C / methanol; acetic acid / 60 h / 3040 Torr

8: 200 mg / POCl₃ / pyridine; CHCl₃ / 7 h / Heating

9: 1) borane-dimethyl sulfide complex, 2) 30 percent H₂O₂ / 1) dry THF, 0-5 deg C, 8.5 h; room temperature, 12 h, 2) 2.5 N aqueous NaOH, room temperature, 1 h; reflux, 1.5 h

10: 76 percent / concentrated H₂SO₄, Jones reagent / acetic acid / 1 h / 20 °C

11: 87 percent / 10 h / 60 - 65 °C

12: 99 percent / lithium bronze reagent (from Li and liquid NH₃), t-butyl alcohol / tetrahydrofuran / 0.5 h / Ambient temperature

13: 74 percent / H₂ / 10 percent Pd on C / ethanol; acetic acid / 0.5 h / 760 Torr

14: 95 percent hydrazine / ethanol / 4 h / 20 °C

15: 72 percent / Et₃N / CH₂Cl₂ / 1) 0 deg C, 15 min, 2) 20 deg C, 3 h

With hydrogenchloride; jones reagent; ethylenediaminetetraacetic acid; dimethylsulfide borane complex; lithium bronze reagent (from Li and liquid NH₃); sulfuric acid; sulfur trioxide; mercury(II) diacetate; hydrogen; dihydrogen peroxide; toluene-4-sulfonic acid; hydrazine hydrate; acetic acid; triethylamine; tert-butyl alcohol; trichlorophosphate; palladium on activated charcoal; platinum on activated charcoal; In tetrahydrofuran; pyridine; methanol; sodium hydroxide; diethyl ether; ethanol; dichloromethane; chloroform; water; acetic acid; isopropyl alcohol; xylene;
DOI:10.1021/jo00186a029