(1'S)-(3'R)-2-(3'-hydroxy-2',2'-dimethyl-6'-methylene-cyclohexyl)-ethyl acetate

Base Information

• Chemical Name: (1'S)-(3'R)-2-(3'-hydroxy-2',2'-dimethyl-6'-methylene-cyclohexyl)-ethyl acetate
• CAS No.: 172958-85-9
• Molecular Formula: C₁₃H₂₂O₃
• Molecular Weight: 226.316
• Mol file: 172958-85-9.mol

Synonyms:(1'S)-(3'R)-2-(3'-hydroxy-2',2'-dimethyl-6'-methylene-cyclohexyl)-ethyl acetate

Chemical Property of (1'S)-(3'R)-2-(3'-hydroxy-2',2'-dimethyl-6'-methylene-cyclohexyl)-ethyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1'S)-(3'R)-2-(3'-hydroxy-2',2'-dimethyl-6'-methylene-cyclohexyl)-ethyl acetate

There total 10 articles about (1'S)-(3'R)-2-(3'-hydroxy-2',2'-dimethyl-6'-methylene-cyclohexyl)-ethyl acetate 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: 83.0%

Acetic acid (Z)-6-((R)-3,3-dimethyl-oxiranyl)-4-trimethylsilanylmethyl-hex-3-enyl ester (172958-86-0) → (1'S)-(3'R)-2-(3'-hydroxy-2',2'-dimethyl-6'-methylene-cyclohexyl)-ethyl acetate (172958-85-9)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 1h;

DOI:10.1016/0957-4166(95)00371-1

Reference yield:

1-bromo-4-methylpent-3-ene (2270-59-9) → (1'S)-(3'R)-2-(3'-hydroxy-2',2'-dimethyl-6'-methylene-cyclohexyl)-ethyl acetate (172958-85-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 55 percent / AD-mix-α, MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C

2: pyridinium p-toluenesulphonate / CH₂Cl₂ / 4 h / 25 °C

3: KI / dimethylformamide / 15 h / 50 °C

4: 1.) t-BuLi / 1.) THF, pentane, from -50 deg C to 0 deg C, 2.) THF, pentane, 25 deg C, 3 h

5: 1.) <1,3-bis(triphenylphosphine)propane>NiCl₂ / 1.) C₆H₆, Et₂O, 25 deg C, 20 min, 2.) C₆H₆, reflux, 6 h

6: 55 percent / DMAP / CH₂Cl₂ / 2 h / 25 °C

7: 34 percent / CF₃CO₂H / tetrahydrofuran; H₂O / 6 h / 25 °C

8: 1.) MsCl, Et₃N, 2.) MeONa / 1.) CH₂Cl₂, -10 deg C, 30 min, 2.) MeOH, -10 deg C, 2 h

9: 100 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / 25 °C

10: 83 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / -78 °C

With dmap; AD-mix-α; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); methanesulfonamide; boron trifluoride diethyl etherate; tert.-butyl lithium; sodium methylate; pyridinium p-toluenesulfonate; methanesulfonyl chloride; triethylamine; trifluoroacetic acid; potassium iodide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1016/0957-4166(95)00371-1

Reference yield:

(4'S)-2-(2',2',5',5'-tetramethyl-<1',3'>dioxolan-4'-yl)-ethanol (67985-68-6) → (1'S)-(3'R)-2-(3'-hydroxy-2',2'-dimethyl-6'-methylene-cyclohexyl)-ethyl acetate (172958-85-9)

Guidance literature:

Multi-step reaction with 9 steps

1: Et₃N / CH₂Cl₂ / 0.33 h

2: NaI / acetone / 0.75 h / Heating

3: 1.) t-BuLi / 1.) THF, pentane, from -50 deg C to 0 deg C, 2.) THF, pentane, 25 deg C, 3 h

4: 1.) <1,3-bis(triphenylphosphine)propane>NiCl₂ / 1.) C₆H₆, Et₂O, 25 deg C, 20 min, 2.) C₆H₆, reflux, 6 h

5: 55 percent / DMAP / CH₂Cl₂ / 2 h / 25 °C

6: 34 percent / CF₃CO₂H / tetrahydrofuran; H₂O / 6 h / 25 °C

7: 1.) MsCl, Et₃N, 2.) MeONa / 1.) CH₂Cl₂, -10 deg C, 30 min, 2.) MeOH, -10 deg C, 2 h

8: 100 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / 25 °C

9: 83 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / -78 °C

With dmap; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); boron trifluoride diethyl etherate; tert.-butyl lithium; sodium methylate; methanesulfonyl chloride; triethylamine; trifluoroacetic acid; sodium iodide; In tetrahydrofuran; dichloromethane; water; acetone;

DOI:10.1016/0957-4166(95)00371-1

upstream raw materials:

Acetic acid (Z)-6-((R)-3,3-dimethyl-oxiranyl)-4-trimethylsilanylmethyl-hex-3-enyl ester

1-bromo-4-methylpent-3-ene

(4'S)-2-(2',2',5',5'-tetramethyl-<1',3'>dioxolan-4'-yl)-ethanol

(5S)-5-bromo-2-methyl-pentane-2,3-diol

Downstream raw materials:

(1'R)-2-(2',2'-dimethyl-6'-methylene-cyclohexyl)-ethanol