4aα-<2-(benzyloxy)ethyl>-7β-hydroxy-1-(methoxycarbonyl)-7α-<2-(trimethylacetamido)benzoyl>-1,2,4a,5,6,7,8a-octahydro-8H-quinolin-8-one

Base Information

• Chemical Name: 4aα-<2-(benzyloxy)ethyl>-7β-hydroxy-1-(methoxycarbonyl)-7α-<2-(trimethylacetamido)benzoyl>-1,2,4a,5,6,7,8a-octahydro-8H-quinolin-8-one
• CAS No.: 131685-25-1
• Molecular Formula: C₃₁H₃₈N₂O₆
• Molecular Weight: 534.653

Synonyms:4aα-<2-(benzyloxy)ethyl>-7β-hydroxy-1-(methoxycarbonyl)-7α-<2-(trimethylacetamido)benzoyl>-1,2,4a,5,6,7,8a-octahydro-8H-quinolin-8-one

Chemical Property of 4aα-<2-(benzyloxy)ethyl>-7β-hydroxy-1-(methoxycarbonyl)-7α-<2-(trimethylacetamido)benzoyl>-1,2,4a,5,6,7,8a-octahydro-8H-quinolin-8-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4aα-<2-(benzyloxy)ethyl>-7β-hydroxy-1-(methoxycarbonyl)-7α-<2-(trimethylacetamido)benzoyl>-1,2,4a,5,6,7,8a-octahydro-8H-quinolin-8-one

There total 19 articles about 4aα-<2-(benzyloxy)ethyl>-7β-hydroxy-1-(methoxycarbonyl)-7α-<2-(trimethylacetamido)benzoyl>-1,2,4a,5,6,7,8a-octahydro-8H-quinolin-8-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:

9-(2-hydroxyethyl)-1,4-dioxaspiro<4.4>nonane (54154-07-3) → 4aα-<2-(benzyloxy)ethyl>-7β-hydroxy-1-(methoxycarbonyl)-7α-<2-(trimethylacetamido)benzoyl>-1,2,4a,5,6,7,8a-octahydro-8H-quinolin-8-one (131685-25-1)

Guidance literature:

Multi-step reaction with 12 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, a) -70 deg C 1 h, b) 0 deg C, 1 h

With sodium hydroxide; sodium periodate; n-butyllithium; oxalyl dichloride; borane; 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; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; toluene; butanone;

Reference yield:

ethyl (2-oxocyclopentyl)acetate (20826-94-2) → 4aα-<2-(benzyloxy)ethyl>-7β-hydroxy-1-(methoxycarbonyl)-7α-<2-(trimethylacetamido)benzoyl>-1,2,4a,5,6,7,8a-octahydro-8H-quinolin-8-one (131685-25-1)

Guidance literature:

Multi-step reaction with 14 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, a) -70 deg C 1 h, b) 0 deg C, 1 h

With sodium hydroxide; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; borane; 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; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; toluene; butanone;

Reference yield:

1,4-Dioxaspiro<4.4>nonan-6-essigsaeure-ethylester (82253-44-9) → 4aα-<2-(benzyloxy)ethyl>-7β-hydroxy-1-(methoxycarbonyl)-7α-<2-(trimethylacetamido)benzoyl>-1,2,4a,5,6,7,8a-octahydro-8H-quinolin-8-one (131685-25-1)

Guidance literature:

Multi-step reaction with 13 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, a) -70 deg C 1 h, b) 0 deg C, 1 h

With sodium hydroxide; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; borane; 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; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; toluene; butanone;

upstream raw materials:

2-<2-(trimethylacetamido)phenyl>-2-<(trimethylsilyl)oxy>acetonitrile

4aα-<2-(benzyloxy)ethyl>-1-(methoxycarbonyl)-1,2,4a,5,6,7aα-hexahydro-7H-1-pyrindin-7-one

9-(2-hydroxyethyl)-1,4-dioxaspiro<4.4>nonane

ethyl (2-oxocyclopentyl)acetate

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