2,2-Dimethyl-propionic acid (S)-5-(1,3-dimethyl-imidazolidin-2-yl)-5-hydroxy-2,4,4-trimethyl-3-oxo-cyclohex-1-enyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (S)-5-(1,3-dimethyl-imidazolidin-2-yl)-5-hydroxy-2,4,4-trimethyl-3-oxo-cyclohex-1-enyl ester
• CAS No.: 162084-41-5
• Molecular Formula: C₁₉H₃₂N₂O₄
• Molecular Weight: 352.474
• Mol file: 162084-41-5.mol

Synonyms:2,2-Dimethyl-propionic acid (S)-5-(1,3-dimethyl-imidazolidin-2-yl)-5-hydroxy-2,4,4-trimethyl-3-oxo-cyclohex-1-enyl ester

Chemical Property of 2,2-Dimethyl-propionic acid (S)-5-(1,3-dimethyl-imidazolidin-2-yl)-5-hydroxy-2,4,4-trimethyl-3-oxo-cyclohex-1-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (S)-5-(1,3-dimethyl-imidazolidin-2-yl)-5-hydroxy-2,4,4-trimethyl-3-oxo-cyclohex-1-enyl ester

There total 12 articles about 2,2-Dimethyl-propionic acid (S)-5-(1,3-dimethyl-imidazolidin-2-yl)-5-hydroxy-2,4,4-trimethyl-3-oxo-cyclohex-1-enyl 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:

2,2-Dimethyl-propionic acid 5-formyl-2,4,4-trimethyl-3-oxo-cyclohex-1-enyl ester (160147-03-5) → 2,2-Dimethyl-propionic acid (S)-5-(1,3-dimethyl-imidazolidin-2-yl)-5-hydroxy-2,4,4-trimethyl-3-oxo-cyclohex-1-enyl ester (162084-41-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 71 percent / DBU; DMAP / CH₂Cl₂ / 4 h / -78 - 20 °C

2: K₂OsO₂(OH)4; K₂Fe(CN)6; DHQ-PHN / K₂CO₃ / 2-methyl-propan-2-ol / 11 h / 0 °C

3: benzene / 0.5 h / Heating

With dmap; DHQ-PHN; potassium dioxotetrahydroxoosmate(VI); K₂Fe(CN)6; 1,8-diazabicyclo[5.4.0]undec-7-ene; potassium carbonate; In dichloromethane; tert-butyl alcohol; benzene; 1: Condensation / 2: dihydroxylation / 3: cyclocondensation;

DOI:10.1021/ja9939439

Reference yield:

(Z)-6-(Tetrahydro-pyran-2-yloxy)-hex-4-en-3-ol (87071-01-0) → 2,2-Dimethyl-propionic acid (S)-5-(1,3-dimethyl-imidazolidin-2-yl)-5-hydroxy-2,4,4-trimethyl-3-oxo-cyclohex-1-enyl ester (162084-41-5)

Guidance literature:

Multi-step reaction with 9 steps

1: (COCl)2; DMSO / CH₂Cl₂ / 10 h / -78 - 20 °C

2: tetrahydrofuran / 1 h / -78 - 0 °C

3: tBuOK / diethyl ether / 3 h / 0 °C

4: CH₂Cl₂ / 20 °C

5: p-TsOH / methanol / 3 h / 20 °C

6: 92 percent / (COCl)2; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

7: 71 percent / DBU; DMAP / CH₂Cl₂ / 4 h / -78 - 20 °C

8: K₂OsO₂(OH)4; K₂Fe(CN)6; DHQ-PHN / K₂CO₃ / 2-methyl-propan-2-ol / 11 h / 0 °C

9: benzene / 0.5 h / Heating

With dmap; oxalyl dichloride; DHQ-PHN; potassium dioxotetrahydroxoosmate(VI); K₂Fe(CN)6; potassium tert-butylate; toluene-4-sulfonic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; potassium carbonate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; tert-butyl alcohol; benzene; 1: Swern oxidation / 2: Condensation / 3: Cyclization / 4: Esterification / 5: cleavage / 6: Swern oxidation / 7: Condensation / 8: dihydroxylation / 9: cyclocondensation;

DOI:10.1021/ja9939439

Reference yield:

1-ethyl-4-(tetrahydro-2-pyranyloxy)-2-butyn-1-ol (14092-31-0) → 2,2-Dimethyl-propionic acid (S)-5-(1,3-dimethyl-imidazolidin-2-yl)-5-hydroxy-2,4,4-trimethyl-3-oxo-cyclohex-1-enyl ester (162084-41-5)

Guidance literature:

Multi-step reaction with 10 steps

1: H₂ / Lindlar's catalyst / hexane / 7 h / 20 °C

2: (COCl)2; DMSO / CH₂Cl₂ / 10 h / -78 - 20 °C

3: tetrahydrofuran / 1 h / -78 - 0 °C

4: tBuOK / diethyl ether / 3 h / 0 °C

5: CH₂Cl₂ / 20 °C

6: p-TsOH / methanol / 3 h / 20 °C

7: 92 percent / (COCl)2; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

8: 71 percent / DBU; DMAP / CH₂Cl₂ / 4 h / -78 - 20 °C

9: K₂OsO₂(OH)4; K₂Fe(CN)6; DHQ-PHN / K₂CO₃ / 2-methyl-propan-2-ol / 11 h / 0 °C

10: benzene / 0.5 h / Heating

With dmap; oxalyl dichloride; DHQ-PHN; potassium dioxotetrahydroxoosmate(VI); K₂Fe(CN)6; potassium tert-butylate; hydrogen; toluene-4-sulfonic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; Lindlar's catalyst; potassium carbonate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; tert-butyl alcohol; benzene; 1: Catalytic hydrogenation / 2: Swern oxidation / 3: Condensation / 4: Cyclization / 5: Esterification / 6: cleavage / 7: Swern oxidation / 8: Condensation / 9: dihydroxylation / 10: cyclocondensation;

DOI:10.1021/ja9939439

upstream raw materials:

2,2-Dimethyl-propionic acid 2,4,4-trimethyl-3-oxo-5-[1-triisopropylsilanyloxy-meth-(E)-ylidene]-cyclohex-1-enyl ester

N,N`-dimethylethylenediamine

2,2-Dimethyl-propionic acid 5-[1-(tert-butyl-dimethyl-silanyloxy)-meth-(E)-ylidene]-2,4,4-trimethyl-3-oxo-cyclohex-1-enyl ester

2,2-Dimethyl-propionic acid (S)-5-formyl-5-hydroxy-2,4,4-trimethyl-3-oxo-cyclohex-1-enyl ester

Downstream raw materials:

(S)-1-Hydroxy-4,6,6-trimethyl-5-oxo-3-triisopropylsilanyloxy-cyclohex-3-enecarbaldehyde