(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

Base Information

Chemical Name:(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
CAS No.:160146-81-6
Molecular Formula:C₃₁H₄₄O₄
Molecular Weight:480.688
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 20 articles about (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 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: 56.0%

: 160146-80-5
(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

: (1S,4S,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

: 160146-81-6
(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

Guidance literature:: With acetyl chloride; lithium diisopropyl amide; 1.) THF, -50 deg C, 2.) MeOH, -80 deg C, 10 min;
DOI:10.1021/jo00099a002

Reference yield:

: 65253-04-5
(-)-8-phenylmenthol

: 160146-81-6
(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

Guidance literature:: Multi-step reaction with 8 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

8: 56 percent / LDA, AcCl / 1.) THF, -50 deg C, 2.) MeOH, -80 deg C, 10 min

With dmap; sodium periodate; osmium(VIII) oxide; formic acid; tert.-butyl lithium; triethylamine; acetyl chloride; lithium diisopropyl amide; palladium(II) acetylacetonate; tributylphosphine; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; acetone; benzene;
DOI:10.1021/jo00099a002

Reference yield:

: 765-69-5
2-Methylcyclopentane-1,3-dione

: 160146-81-6
(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

Guidance literature:: Multi-step reaction with 15 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

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; acetyl chloride; sodium iodide; lithium diisopropyl amide; 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