Benzoic acid (1S,3aS,4R,7aS)-7a-methyl-1-(2-methyl-[1,3]dioxolan-2-yl)-octahydro-inden-4-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (1S,3aS,4R,7aS)-7a-methyl-1-(2-methyl-[1,3]dioxolan-2-yl)-octahydro-inden-4-ylmethyl ester
• CAS No.: 1027563-72-9
• Molecular Formula: C₂₂H₃₀O₄
• Molecular Weight: 358.478
• Mol file: 1027563-72-9.mol

Synonyms:Benzoic acid (1S,3aS,4R,7aS)-7a-methyl-1-(2-methyl-[1,3]dioxolan-2-yl)-octahydro-inden-4-ylmethyl ester

Chemical Property of Benzoic acid (1S,3aS,4R,7aS)-7a-methyl-1-(2-methyl-[1,3]dioxolan-2-yl)-octahydro-inden-4-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (1S,3aS,4R,7aS)-7a-methyl-1-(2-methyl-[1,3]dioxolan-2-yl)-octahydro-inden-4-ylmethyl ester

There total 23 articles about Benzoic acid (1S,3aS,4R,7aS)-7a-methyl-1-(2-methyl-[1,3]dioxolan-2-yl)-octahydro-inden-4-ylmethyl ester 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:

Benzoic acid (1S,4R,7aR)-7a-methyl-1-(2-methyl-[1,3]dioxolan-2-yl)-2,4,5,6,7,7a-hexahydro-1H-inden-4-ylmethyl ester (160146-85-0) → Benzoic acid (1S,3aS,4R,7aS)-7a-methyl-1-(2-methyl-[1,3]dioxolan-2-yl)-octahydro-inden-4-ylmethyl ester (1027563-72-9)

Guidance literature:

With hydrogen; sodium hydrogencarbonate; palladium on activated charcoal; for 14h; under 760 Torr; Ambient temperature;

DOI:10.1021/jo00099a002

Reference yield:

2-Methylcyclopentane-1,3-dione (765-69-5) → Benzoic acid (1S,3aS,4R,7aS)-7a-methyl-1-(2-methyl-[1,3]dioxolan-2-yl)-octahydro-inden-4-ylmethyl ester (1027563-72-9)

Guidance literature:

Multi-step reaction with 18 steps

1: 88 percent / Pd(OAc)2/PPh₃ / tetrahydrofuran / 6 h / Ambient temperature

2: 95 percent / TMSOTf / 10 h / -2 - 0 °C

3: 1.) BH₃*Me₂S, 2.) H₂O₂, 3 N NaOH / 1.) THF, 0 deg C to r.t., 4 h, 2.) r.t. 14 h

4: Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

5: NaI, NaHCO₃ / acetone / 2.5 h / Heating

6: 70 percent / NaH / dimethylformamide / 13 h / Ambient temperature

7: 95 percent / Amberlyst-15 / acetone / 14 h / Ambient temperature

8: 80 percent / t-BuOK / tetrahydrofuran / 0.5 h / -80 °C

9: 56 percent / diethyl ether / -80 °C

10: 95 percent / t-BuLi / tetrahydrofuran / 14 h

11: 93 percent / HCO₂H, Et₃N / Pd(acac)2/Bu₃P / benzene / 3 h / Ambient temperature

12: 61 percent / OsO₄ / dioxane; H₂O / 2 h / Ambient temperature

13: NaIO₄ / acetone / 3 h / Ambient temperature

14: 95 percent / TMSOTf / CH₂Cl₂ / 3 h / -25 °C

15: 56 percent / LDA, AcCl / 1.) THF, -50 deg C, 2.) MeOH, -80 deg C, 10 min

16: LiAlH₄ / diethyl ether

17: 82 percent / pyridine

18: H₂, NaHCO₃ / Pd/C / 14 h / 760 Torr / Ambient temperature

With pyridine; sodium hydroxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; formic acid; dimethylsulfide borane complex; potassium tert-butylate; hydrogen; dihydrogen peroxide; tert.-butyl lithium; sodium hydride; sodium hydrogencarbonate; triethylamine; acetyl chloride; sodium iodide; lithium diisopropyl amide; palladium diacetate; palladium(II) acetylacetonate; palladium on activated charcoal; amberlyst-15; tributylphosphine; trimethylsilyl trifluoromethanesulfonate; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1021/jo00099a002

Reference yield:

6-allyl-6-methyl-1,4,8,11-tetraoxadispiro[4.1.4.2]tridecane (70833-73-7) → Benzoic acid (1S,3aS,4R,7aS)-7a-methyl-1-(2-methyl-[1,3]dioxolan-2-yl)-octahydro-inden-4-ylmethyl ester (1027563-72-9)

Guidance literature:

Multi-step reaction with 16 steps

1: 1.) BH₃*Me₂S, 2.) H₂O₂, 3 N NaOH / 1.) THF, 0 deg C to r.t., 4 h, 2.) r.t. 14 h

2: Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

3: NaI, NaHCO₃ / acetone / 2.5 h / Heating

4: 70 percent / NaH / dimethylformamide / 13 h / Ambient temperature

5: 95 percent / Amberlyst-15 / acetone / 14 h / Ambient temperature

6: 80 percent / t-BuOK / tetrahydrofuran / 0.5 h / -80 °C

7: 56 percent / diethyl ether / -80 °C

8: 95 percent / t-BuLi / tetrahydrofuran / 14 h

9: 93 percent / HCO₂H, Et₃N / Pd(acac)2/Bu₃P / benzene / 3 h / Ambient temperature

10: 61 percent / OsO₄ / dioxane; H₂O / 2 h / Ambient temperature

11: NaIO₄ / acetone / 3 h / Ambient temperature

12: 95 percent / TMSOTf / CH₂Cl₂ / 3 h / -25 °C

13: 56 percent / LDA, AcCl / 1.) THF, -50 deg C, 2.) MeOH, -80 deg C, 10 min

14: LiAlH₄ / diethyl ether

15: 82 percent / pyridine

16: H₂, NaHCO₃ / Pd/C / 14 h / 760 Torr / Ambient temperature

With pyridine; sodium hydroxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; formic acid; dimethylsulfide borane complex; potassium tert-butylate; hydrogen; dihydrogen peroxide; tert.-butyl lithium; sodium hydride; sodium hydrogencarbonate; triethylamine; acetyl chloride; sodium iodide; lithium diisopropyl amide; palladium(II) acetylacetonate; palladium on activated charcoal; amberlyst-15; tributylphosphine; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1021/jo00099a002

upstream raw materials:

Benzoic acid (1S,4R,7aR)-7a-methyl-1-(2-methyl-[1,3]dioxolan-2-yl)-2,4,5,6,7,7a-hexahydro-1H-inden-4-ylmethyl ester

2-Methylcyclopentane-1,3-dione

6-allyl-6-methyl-1,4,8,11-tetraoxadispiro[4.1.4.2]tridecane

2-allyl-2-methyl-1,3-cyclopentanedione