(+)-3-hydroxycuparene

Base Information

• Chemical Name: (+)-3-hydroxycuparene
• CAS No.: 252285-40-8
• Molecular Formula: C₁₅H₂₂O
• Molecular Weight: 218.339
• Mol file: 252285-40-8.mol

Synonyms:(+)-3-hydroxycuparene

Chemical Property of (+)-3-hydroxycuparene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-3-hydroxycuparene

There total 12 articles about (+)-3-hydroxycuparene 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:

D-(+)-camphoric acid (124-83-4) → (+)-3-hydroxycuparene (252285-40-8)

Guidance literature:

Multi-step reaction with 12 steps

1: 92 percent / H₂SO₄ / 4 h

2: 89 percent / KOH / methanol / 72 h / Heating

3: 78 percent / Pb(OAc)4; Cu(OAc)2*H₂O; pyridine / benzene / 2 h / Heating

4: LiAlH₄ / diethyl ether / 1 h / 0 °C

5: PySO₃; Et₃N / dimethylsulfoxide

6: 19 g / CHCl₃ / 30 h / Heating

7: DIBAH / tetrahydrofuran / 1 h / 0 °C

8: 10.4 g / MnO₂ / CH₂Cl₂ / 24 h / Heating

9: 75 percent / CHCl₃ / 36 Torr / Heating

10: Et₃N / tetrahydrofuran / 20 h / 2 °C

11: LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

12: 900 mg / H₂ / Pd/C / ethyl acetate / 36 h

With pyridine; lead(IV) acetate; manganese(IV) oxide; potassium hydroxide; lithium aluminium tetrahydride; copper diacetate; sulfuric acid; hydrogen; sulfur trioxide pyridine complex; diisobutylaluminium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; dimethyl sulfoxide; ethyl acetate; benzene; 1: Esterification / 2: Hydrolysis / 3: Elimination / 4: Reduction / 5: Oxidation / 6: Wittig reaction / 7: Reduction / 8: Oxidation / 9: Wittig reaction / 10: Cyclization / 11: Reduction / 12: Reduction;

DOI:10.1021/jo9909148

Reference yield:

(1S,3R)-3-(methoxycarbonyl)-2,2,3-trimethylcyclopentanecarboxylic acid (29606-94-8) → (+)-3-hydroxycuparene (252285-40-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 78 percent / Pb(OAc)4; Cu(OAc)2*H₂O; pyridine / benzene / 2 h / Heating

2: LiAlH₄ / diethyl ether / 1 h / 0 °C

3: PySO₃; Et₃N / dimethylsulfoxide

4: 19 g / CHCl₃ / 30 h / Heating

5: DIBAH / tetrahydrofuran / 1 h / 0 °C

6: 10.4 g / MnO₂ / CH₂Cl₂ / 24 h / Heating

7: 75 percent / CHCl₃ / 36 Torr / Heating

8: Et₃N / tetrahydrofuran / 20 h / 2 °C

9: LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

10: 900 mg / H₂ / Pd/C / ethyl acetate / 36 h

With pyridine; lead(IV) acetate; manganese(IV) oxide; lithium aluminium tetrahydride; copper diacetate; hydrogen; sulfur trioxide pyridine complex; diisobutylaluminium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform; dimethyl sulfoxide; ethyl acetate; benzene; 1: Elimination / 2: Reduction / 3: Oxidation / 4: Wittig reaction / 5: Reduction / 6: Oxidation / 7: Wittig reaction / 8: Cyclization / 9: Reduction / 10: Reduction;

DOI:10.1021/jo9909148

Reference yield:

dimethyl (1R,3S)-1,2,2-trimethylcyclopentane-1,3-dicarboxylate (15797-21-4) → (+)-3-hydroxycuparene (252285-40-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 89 percent / KOH / methanol / 72 h / Heating

2: 78 percent / Pb(OAc)4; Cu(OAc)2*H₂O; pyridine / benzene / 2 h / Heating

3: LiAlH₄ / diethyl ether / 1 h / 0 °C

4: PySO₃; Et₃N / dimethylsulfoxide

5: 19 g / CHCl₃ / 30 h / Heating

6: DIBAH / tetrahydrofuran / 1 h / 0 °C

7: 10.4 g / MnO₂ / CH₂Cl₂ / 24 h / Heating

8: 75 percent / CHCl₃ / 36 Torr / Heating

9: Et₃N / tetrahydrofuran / 20 h / 2 °C

10: LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

11: 900 mg / H₂ / Pd/C / ethyl acetate / 36 h

With pyridine; lead(IV) acetate; manganese(IV) oxide; potassium hydroxide; lithium aluminium tetrahydride; copper diacetate; hydrogen; sulfur trioxide pyridine complex; diisobutylaluminium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; dimethyl sulfoxide; ethyl acetate; benzene; 1: Hydrolysis / 2: Elimination / 3: Reduction / 4: Oxidation / 5: Wittig reaction / 6: Reduction / 7: Oxidation / 8: Wittig reaction / 9: Cyclization / 10: Reduction / 11: Reduction;

DOI:10.1021/jo9909148

upstream raw materials:

D-(+)-camphoric acid

(R)-1,2,2-trimethylcyclopent-3-enecarboxylic acid methyl ester

(1S,3R)-3-(methoxycarbonyl)-2,2,3-trimethylcyclopentanecarboxylic acid

dimethyl (1R,3S)-1,2,2-trimethylcyclopentane-1,3-dicarboxylate

Downstream raw materials:

cuparene

Refernces