methyl (6aβ,13bα,13aα)-13a-<2-(benzyloxy)ethyl>-5,6,11,13,13a,13b-hexahydro-3H-cyclopentindolo<2,3-a>quinolizine-12-carboxylate

Base Information

Chemical Name:methyl (6aβ,13bα,13aα)-13a-<2-(benzyloxy)ethyl>-5,6,11,13,13a,13b-hexahydro-3H-cyclopentindolo<2,3-a>quinolizine-12-carboxylate
CAS No.:131685-30-8
Molecular Formula:C₂₈H₃₀N₂O₃
Molecular Weight:442.558
Hs Code.:

methyl (6aβ,13bα,13aα)-13a-<2-(benzyloxy)ethyl>-5,6,11,13,13a,13b-hexahydro-3H-cyclopent<ij>indolo<2,3-a>quinolizine-12-carboxylate

Synonyms:methyl (6aβ,13bα,13aα)-13a-<2-(benzyloxy)ethyl>-5,6,11,13,13a,13b-hexahydro-3H-cyclopentindolo<2,3-a>quinolizine-12-carboxylate

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Chemical Property of methyl (6aβ,13bα,13aα)-13a-<2-(benzyloxy)ethyl>-5,6,11,13,13a,13b-hexahydro-3H-cyclopentindolo<2,3-a>quinolizine-12-carboxylate

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Technology Process of methyl (6aβ,13bα,13aα)-13a-<2-(benzyloxy)ethyl>-5,6,11,13,13a,13b-hexahydro-3H-cyclopentindolo<2,3-a>quinolizine-12-carboxylate

There total 19 articles about methyl (6aβ,13bα,13aα)-13a-<2-(benzyloxy)ethyl>-5,6,11,13,13a,13b-hexahydro-3H-cyclopentindolo<2,3-a>quinolizine-12-carboxylate 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:

: 54154-07-3
9-(2-hydroxyethyl)-1,4-dioxaspiro<4.4>nonane

: 131685-30-8
methyl (6aβ,13bα,13aα)-13a-<2-(benzyloxy)ethyl>-5,6,11,13,13a,13b-hexahydro-3H-cyclopentindolo<2,3-a>quinolizine-12-carboxylate

Guidance literature:: Multi-step reaction with 17 steps

1: 99 percent / 50percent aq. NaOH, (n-Bu)4NHSO₄ / 0.75 h / 23 °C

2: 16.6 g / water, pyridine p-toluenesulfonate (PPTS) / acetone / 16 h / Heating

3: Et₃N / dimethylformamide / 96 h / 130 °C

4: ZnBr₂ / CH₂Cl₂ / 1 h / 23 °C

5: NaHCO₃, NaI / butan-2-one / 1.) 23 deg C, 22 h, 2.) reflux, 20 h

6: liq. NH₃ / CHCl₃ / 72 h / 5171.5 Torr / Ambient temperature

7: KHCO₃ / CHCl₃ / 14 h / 23 °C

8: 1.) BH₃, 2.) 3 M NaOH, 30percent aq. H₂O₂ / 1.) THF, 23 deg C, 45 min, 2.) 23 deg C, 2 h

9: 10.6 g / oxalyl chloride, DMSO / CH₂Cl₂ / 3 h / -60 °C

10: NaIO₄ / H₂O; methanol / 72 h / 23 °C

11: Et₃N / toluene / 72 h / Heating

12: 1.) n-BuLi / 1.) THF, cyclohexane, -70 deg C, 45 min, 2.) THF, cyclohexane, -70 deg C 4 h

13: 1.) n-BuLi / 1.) THF, hexane, a) -70 deg C, 30 min, b) 23 deg C, 40 min, 2.) THF, hexane, a) -70 deg C, 1 h, b) 23 deg C, 48 h

14: 62 percent / KOH / H₂O; ethanol / 16 h / 210 °C

15: 100 percent / Na₂SO₄ / toluene / 24 h / 23 °C

16: Na₂SO₄, camphorsulfonic acid / benzene / 2.5 h / Heating

17: 1.) THF, cyclohexane, -70 deg C, 1.5 h, 2.) THF, cyclohexane, -70 deg C, 2 h

With potassium hydroxide; sodium hydroxide; sodium periodate; n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; borane; ammonia; water; dihydrogen peroxide; tetra(n-butyl)ammonium hydrogensulfate; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium hydrogencarbonate; dimethyl sulfoxide; sodium sulfate; triethylamine; sodium iodide; zinc dibromide; In methanol; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; toluene; butanone; benzene;

Reference yield:

: 20826-94-2
ethyl (2-oxocyclopentyl)acetate

: 131685-30-8
methyl (6aβ,13bα,13aα)-13a-<2-(benzyloxy)ethyl>-5,6,11,13,13a,13b-hexahydro-3H-cyclopentindolo<2,3-a>quinolizine-12-carboxylate

Guidance literature:: Multi-step reaction with 19 steps

1: 86 percent / pyridine p-toluenesulfonate (PPTS) / toluene / 12 h / Heating

2: 92 percent / LiAlH₄ / diethyl ether / 1.) 0 deg C, 1 h, 2.) 23 deg C, 1 h

3: 99 percent / 50percent aq. NaOH, (n-Bu)4NHSO₄ / 0.75 h / 23 °C

4: 16.6 g / water, pyridine p-toluenesulfonate (PPTS) / acetone / 16 h / Heating

5: Et₃N / dimethylformamide / 96 h / 130 °C

6: ZnBr₂ / CH₂Cl₂ / 1 h / 23 °C

7: NaHCO₃, NaI / butan-2-one / 1.) 23 deg C, 22 h, 2.) reflux, 20 h

8: liq. NH₃ / CHCl₃ / 72 h / 5171.5 Torr / Ambient temperature

9: KHCO₃ / CHCl₃ / 14 h / 23 °C

10: 1.) BH₃, 2.) 3 M NaOH, 30percent aq. H₂O₂ / 1.) THF, 23 deg C, 45 min, 2.) 23 deg C, 2 h

11: 10.6 g / oxalyl chloride, DMSO / CH₂Cl₂ / 3 h / -60 °C

12: NaIO₄ / H₂O; methanol / 72 h / 23 °C

13: Et₃N / toluene / 72 h / Heating

14: 1.) n-BuLi / 1.) THF, cyclohexane, -70 deg C, 45 min, 2.) THF, cyclohexane, -70 deg C 4 h

15: 1.) n-BuLi / 1.) THF, hexane, a) -70 deg C, 30 min, b) 23 deg C, 40 min, 2.) THF, hexane, a) -70 deg C, 1 h, b) 23 deg C, 48 h

16: 62 percent / KOH / H₂O; ethanol / 16 h / 210 °C

17: 100 percent / Na₂SO₄ / toluene / 24 h / 23 °C

18: Na₂SO₄, camphorsulfonic acid / benzene / 2.5 h / Heating

19: 1.) THF, cyclohexane, -70 deg C, 1.5 h, 2.) THF, cyclohexane, -70 deg C, 2 h

With potassium hydroxide; sodium hydroxide; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; borane; ammonia; water; dihydrogen peroxide; tetra(n-butyl)ammonium hydrogensulfate; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium hydrogencarbonate; dimethyl sulfoxide; sodium sulfate; triethylamine; sodium iodide; zinc dibromide; In methanol; diethyl ether; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; toluene; butanone; benzene;

Reference yield:

: 82253-44-9
1,4-Dioxaspiro<4.4>nonan-6-essigsaeure-ethylester

: 131685-30-8
methyl (6aβ,13bα,13aα)-13a-<2-(benzyloxy)ethyl>-5,6,11,13,13a,13b-hexahydro-3H-cyclopentindolo<2,3-a>quinolizine-12-carboxylate

Guidance literature:: Multi-step reaction with 18 steps

1: 92 percent / LiAlH₄ / diethyl ether / 1.) 0 deg C, 1 h, 2.) 23 deg C, 1 h

2: 99 percent / 50percent aq. NaOH, (n-Bu)4NHSO₄ / 0.75 h / 23 °C

3: 16.6 g / water, pyridine p-toluenesulfonate (PPTS) / acetone / 16 h / Heating

4: Et₃N / dimethylformamide / 96 h / 130 °C

5: ZnBr₂ / CH₂Cl₂ / 1 h / 23 °C

6: NaHCO₃, NaI / butan-2-one / 1.) 23 deg C, 22 h, 2.) reflux, 20 h

7: liq. NH₃ / CHCl₃ / 72 h / 5171.5 Torr / Ambient temperature

8: KHCO₃ / CHCl₃ / 14 h / 23 °C

9: 1.) BH₃, 2.) 3 M NaOH, 30percent aq. H₂O₂ / 1.) THF, 23 deg C, 45 min, 2.) 23 deg C, 2 h

10: 10.6 g / oxalyl chloride, DMSO / CH₂Cl₂ / 3 h / -60 °C

11: NaIO₄ / H₂O; methanol / 72 h / 23 °C

12: Et₃N / toluene / 72 h / Heating

13: 1.) n-BuLi / 1.) THF, cyclohexane, -70 deg C, 45 min, 2.) THF, cyclohexane, -70 deg C 4 h

14: 1.) n-BuLi / 1.) THF, hexane, a) -70 deg C, 30 min, b) 23 deg C, 40 min, 2.) THF, hexane, a) -70 deg C, 1 h, b) 23 deg C, 48 h

15: 62 percent / KOH / H₂O; ethanol / 16 h / 210 °C

16: 100 percent / Na₂SO₄ / toluene / 24 h / 23 °C

17: Na₂SO₄, camphorsulfonic acid / benzene / 2.5 h / Heating

18: 1.) THF, cyclohexane, -70 deg C, 1.5 h, 2.) THF, cyclohexane, -70 deg C, 2 h

With potassium hydroxide; sodium hydroxide; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; borane; ammonia; water; dihydrogen peroxide; tetra(n-butyl)ammonium hydrogensulfate; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium hydrogencarbonate; dimethyl sulfoxide; sodium sulfate; triethylamine; sodium iodide; zinc dibromide; In methanol; diethyl ether; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; toluene; butanone; benzene;