scopine benzyl ether

Base Information

• Chemical Name: scopine benzyl ether
• CAS No.: 132622-34-5
• Molecular Formula: C₁₅H₁₉NO₂
• Molecular Weight: 245.321
• Mol file: 132622-34-5.mol

Synonyms:

Chemical Property of scopine benzyl ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of scopine benzyl ether

There total 19 articles about scopine benzyl ether 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:

cyclohepta-3,5-dien-1-ol (1121-63-7) → pseudoscopine benzyl ether (132622-34-5,132697-33-7)

Guidance literature:

Multi-step reaction with 10 steps

1: NaH / tetrahydrofuran / 15 h / 50 °C

2: 63 percent / LiCl, p-benzoquinone, glacial acetic acid / Pd(OAc)2 / acetic acid / 36 h

3: 79 percent / dimethylsulfoxide / 3 h / 80 °C

4: 84 percent / 2M NaOH / methanol / 4 h / Heating

5: 94 percent / imidazole / dimethylformamide / 4 h / 0 °C

6: 96 percent / m-CPBA / CHCl₃ / 1) 0 deg C, 1h, 2) 20 deg C, 2h, 3) refrigerator, overnight

7: 95 percent / Bu₄NF / tetrahydrofuran / 20 h / Ambient temperature

8: Et₃N / tetrahydrofuran / 2 h / Ambient temperature

9: K₂CO₃ / methanol / 120 h

10: 1) naphthalene, Na / 1) DME, -78 deg C, 40 min, 2)a) -78 deg C, 15 min, b) r.t., 40 min

With 1H-imidazole; sodium hydroxide; naphthalene; tetrabutyl ammonium fluoride; sodium; sodium hydride; potassium carbonate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; p-benzoquinone; lithium chloride; palladium diacetate; In tetrahydrofuran; methanol; chloroform; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jo00008a037

Reference yield:

cyclohepta-3,5-dien-1-ol (1121-63-7) → scopine benzyl ether (132622-34-5,132697-33-7)

Guidance literature:

Multi-step reaction with 8 steps

1: NaH / tetrahydrofuran / 15 h / 50 °C

2: 63 percent / LiCl, p-benzoquinone, glacial acetic acid / Pd(OAc)2 / acetic acid / 36 h

3: 96 percent / DIBAL / tetrahydrofuran; hexane / 0.75 h / 2 °C

4: 66 percent / Pd(PPh₃)4 / acetonitrile / 4 h

5: 76 percent / LiCl, MsCl, 2,4,6-trimethylpyridine / dimethylformamide / 0 deg C to r.t., overnight

6: 86 percent / m-CPBA / CH₂Cl₂ / 48 h / Ambient temperature

7: 95 percent / K₂CO₃ / methanol / 56 h / Ambient temperature

8: 1) naphthalene, Na / 1) THF, -78 deg C, 30 min

With 2,4,6-trimethyl-pyridine; naphthalene; sodium; sodium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; methanesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; p-benzoquinone; lithium chloride; palladium diacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; hexane; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00008a037

Reference yield:

benzyl bromide (100-39-0) → pseudoscopine benzyl ether (132622-34-5,132697-33-7)

Guidance literature:

Multi-step reaction with 10 steps

1: NaH / tetrahydrofuran / 15 h / 50 °C

2: 63 percent / LiCl, p-benzoquinone, glacial acetic acid / Pd(OAc)2 / acetic acid / 36 h

3: 79 percent / dimethylsulfoxide / 3 h / 80 °C

4: 84 percent / 2M NaOH / methanol / 4 h / Heating

5: 94 percent / imidazole / dimethylformamide / 4 h / 0 °C

6: 96 percent / m-CPBA / CHCl₃ / 1) 0 deg C, 1h, 2) 20 deg C, 2h, 3) refrigerator, overnight

7: 95 percent / Bu₄NF / tetrahydrofuran / 20 h / Ambient temperature

8: Et₃N / tetrahydrofuran / 2 h / Ambient temperature

9: K₂CO₃ / methanol / 120 h

10: 1) naphthalene, Na / 1) DME, -78 deg C, 40 min, 2)a) -78 deg C, 15 min, b) r.t., 40 min

With 1H-imidazole; sodium hydroxide; naphthalene; tetrabutyl ammonium fluoride; sodium; sodium hydride; potassium carbonate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; p-benzoquinone; lithium chloride; palladium diacetate; In tetrahydrofuran; methanol; chloroform; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jo00008a037

upstream raw materials:

cyclohepta-3,5-dien-1-ol

benzyl bromide

6-(benzyloxy)-1,3-cycloheptadiene

1β-acetoxy-4β-chloro-6α-(benzyloxy)-2-cycloheptene

Downstream raw materials:

scopine

pseudoscopine

Refernces