(1S,7aR)-7a-Methyl-1-(2-methyl-[1,3]dioxolan-2-yl)-2,3,5,6,7,7a-hexahydro-1H-indene-4-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Base Information

• Chemical Name: (1S,7aR)-7a-Methyl-1-(2-methyl-[1,3]dioxolan-2-yl)-2,3,5,6,7,7a-hexahydro-1H-indene-4-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester
• CAS No.: 160146-80-5
• Molecular Formula: C₃₁H₄₄O₄
• Molecular Weight: 480.688
• Mol file: 160146-80-5.mol

Synonyms:(1S,7aR)-7a-Methyl-1-(2-methyl-[1,3]dioxolan-2-yl)-2,3,5,6,7,7a-hexahydro-1H-indene-4-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Chemical Property of (1S,7aR)-7a-Methyl-1-(2-methyl-[1,3]dioxolan-2-yl)-2,3,5,6,7,7a-hexahydro-1H-indene-4-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,7aR)-7a-Methyl-1-(2-methyl-[1,3]dioxolan-2-yl)-2,3,5,6,7,7a-hexahydro-1H-indene-4-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

There total 19 articles about (1S,7aR)-7a-Methyl-1-(2-methyl-[1,3]dioxolan-2-yl)-2,3,5,6,7,7a-hexahydro-1H-indene-4-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl 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: 95.0%

2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane (7381-30-8) + (1S,7aR)-1-Acetyl-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-indene-4-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (160146-79-2) → (1S,7aR)-7a-Methyl-1-(2-methyl-[1,3]dioxolan-2-yl)-2,3,5,6,7,7a-hexahydro-1H-indene-4-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (160146-80-5)

Guidance literature:

trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -25 ℃; for 3h;

DOI:10.1021/jo00099a002

Reference yield:

(-)-8-phenylmenthol (65253-04-5) → (1S,7aR)-7a-Methyl-1-(2-methyl-[1,3]dioxolan-2-yl)-2,3,5,6,7,7a-hexahydro-1H-indene-4-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (160146-80-5)

Guidance literature:

Multi-step reaction with 7 steps

1: DMAP / CH₂Cl₂ / 8 h / Heating

2: 56 percent / diethyl ether / -80 °C

3: 95 percent / t-BuLi / tetrahydrofuran / 14 h

4: 93 percent / HCO₂H, Et₃N / Pd(acac)2/Bu₃P / benzene / 3 h / Ambient temperature

5: 61 percent / OsO₄ / dioxane; H₂O / 2 h / Ambient temperature

6: NaIO₄ / acetone / 3 h / Ambient temperature

7: 95 percent / TMSOTf / CH₂Cl₂ / 3 h / -25 °C

With dmap; sodium periodate; osmium(VIII) oxide; formic acid; tert.-butyl lithium; triethylamine; palladium(II) acetylacetonate; tributylphosphine; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; acetone; benzene;

DOI:10.1021/jo00099a002

Reference yield:

2-Methylcyclopentane-1,3-dione (765-69-5) → (1S,7aR)-7a-Methyl-1-(2-methyl-[1,3]dioxolan-2-yl)-2,3,5,6,7,7a-hexahydro-1H-indene-4-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (160146-80-5)

Guidance literature:

Multi-step reaction with 14 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

With sodium hydroxide; sodium periodate; osmium(VIII) oxide; formic acid; dimethylsulfide borane complex; potassium tert-butylate; dihydrogen peroxide; tert.-butyl lithium; sodium hydride; sodium hydrogencarbonate; triethylamine; sodium iodide; palladium diacetate; palladium(II) acetylacetonate; 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

upstream raw materials:

2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane

(1S,7aR)-1-Acetyl-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-indene-4-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

2-Methylcyclopentane-1,3-dione

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

Downstream raw materials:

(1S,4R,7aR)-7a-Methyl-1-(2-methyl-[1,3]dioxolan-2-yl)-2,4,5,6,7,7a-hexahydro-1H-indene-4-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

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

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