(6aα,8aα,8bα)-6a-<2-(benzyloxy)ethyl>-8a-<2-(trimethylacetamido)phenyl>-1,2,3,6a,7,8,8a-heptahydro-4H-cyclopentindolizine-8-carboxylic acid

Base Information

Chemical Name:(6aα,8aα,8bα)-6a-<2-(benzyloxy)ethyl>-8a-<2-(trimethylacetamido)phenyl>-1,2,3,6a,7,8,8a-heptahydro-4H-cyclopentindolizine-8-carboxylic acid
CAS No.:131685-27-3
Molecular Formula:C₃₁H₃₈N₂O₄
Molecular Weight:502.654
Hs Code.:

(6aα,8aα,8bα)-6a-<2-(benzyloxy)ethyl>-8a-<2-(trimethylacetamido)phenyl>-1,2,3,6a,7,8,8a-heptahydro-4H-cyclopent<hi>indolizine-8-carboxylic acid

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Chemical Property of (6aα,8aα,8bα)-6a-<2-(benzyloxy)ethyl>-8a-<2-(trimethylacetamido)phenyl>-1,2,3,6a,7,8,8a-heptahydro-4H-cyclopentindolizine-8-carboxylic acid

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Technology Process of (6aα,8aα,8bα)-6a-<2-(benzyloxy)ethyl>-8a-<2-(trimethylacetamido)phenyl>-1,2,3,6a,7,8,8a-heptahydro-4H-cyclopentindolizine-8-carboxylic acid

There total 24 articles about (6aα,8aα,8bα)-6a-<2-(benzyloxy)ethyl>-8a-<2-(trimethylacetamido)phenyl>-1,2,3,6a,7,8,8a-heptahydro-4H-cyclopentindolizine-8-carboxylic acid 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: 8.0%

: 119146-68-8,119239-80-4
methyl (6aα,8aα,8bα)-6a-<2-(benzyloxy)ethyl>-8a-<2-(trimethylacetamido)phenyl>-1,2,3,6a,7,8,8b-heptahydro-4H-cyclopentindolizine-8-carboxylate

: 131685-27-3,131725-08-1
(6aα,8aα,8bα)-6a-<2-(benzyloxy)ethyl>-8a-<2-(trimethylacetamido)phenyl>-1,2,3,6a,7,8,8a-heptahydro-4H-cyclopentindolizine-8-carboxylic acid

: 119182-74-0,119182-76-2
(6aα,7aα,11aα,13aR^*)-7a-<2-(benzyloxy)ethyl>-6a,7,7a,11a,12,13-hexahydro-10H-indolizino<1',8':2,3,4>cyclopenta<1,2-c>quinolin-6(5H)-one

: 119182-74-0,119182-76-2
(6aβ,7aα,11aα,13aR^*)-7a-<2-(benzyloxy)ethyl>-6a,7,7a,11a,12,13-hexahydro-10H-indolizino<1',8':2,3,4>cyclopenta<1,2-c>quinolin-6(5H)-one

Guidance literature:: With potassium hydroxide; In ethanol; water; 1.) RT, 1 h, 2.) from 50 deg C to 150 deg C, 24,5 h;

Reference yield:

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

: 131685-27-3,131725-08-1
(6aα,8aα,8bα)-6a-<2-(benzyloxy)ethyl>-8a-<2-(trimethylacetamido)phenyl>-1,2,3,6a,7,8,8a-heptahydro-4H-cyclopentindolizine-8-carboxylic acid

Guidance literature:: Multi-step reaction with 18 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: 84 percent / KOH / H₂O; ethanol / 20 h / 130 °C

15: 83 percent / camphorsulfonic acid / benzene / 3 h / Heating

16: 98 percent / 2,4,6-triisopropylphenylsulfonyl azide, (n-Bu)4NBr, 18-crown-6, 66percent aq. KOH / benzene / 1 h / 35 °C

17: diethyl ether / 0.25 h / Irradiation

18: 4 percent / KOH / ethanol; H₂O / 1.) RT, 1 h, 2.) from 50 deg C to 150 deg C, 24,5 h

With potassium hydroxide; sodium hydroxide; sodium periodate; n-butyllithium; oxalyl dichloride; 18-crown-6 ether; camphor-10-sulfonic acid; 2,4,6-Triisopropylbenzenesulfonyl azide; borane; tetrabutylammomium bromide; ammonia; water; dihydrogen peroxide; tetra(n-butyl)ammonium hydrogensulfate; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium hydrogencarbonate; dimethyl sulfoxide; triethylamine; sodium iodide; zinc dibromide; In methanol; diethyl ether; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; toluene; butanone; benzene;

Reference yield:

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

: 131685-27-3,131725-08-1
(6aα,8aα,8bα)-6a-<2-(benzyloxy)ethyl>-8a-<2-(trimethylacetamido)phenyl>-1,2,3,6a,7,8,8a-heptahydro-4H-cyclopentindolizine-8-carboxylic acid

Guidance literature:: Multi-step reaction with 20 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: 84 percent / KOH / H₂O; ethanol / 20 h / 130 °C

17: 83 percent / camphorsulfonic acid / benzene / 3 h / Heating

18: 98 percent / 2,4,6-triisopropylphenylsulfonyl azide, (n-Bu)4NBr, 18-crown-6, 66percent aq. KOH / benzene / 1 h / 35 °C

19: diethyl ether / 0.25 h / Irradiation

20: 4 percent / KOH / ethanol; H₂O / 1.) RT, 1 h, 2.) from 50 deg C to 150 deg C, 24,5 h

With potassium hydroxide; sodium hydroxide; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; 18-crown-6 ether; camphor-10-sulfonic acid; 2,4,6-Triisopropylbenzenesulfonyl azide; borane; tetrabutylammomium bromide; ammonia; water; dihydrogen peroxide; tetra(n-butyl)ammonium hydrogensulfate; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium hydrogencarbonate; dimethyl sulfoxide; triethylamine; sodium iodide; zinc dibromide; In methanol; diethyl ether; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; toluene; butanone; benzene;