(1R,2S,6R,7S,1'R)-5-N-acetyl-(N-1'-phenylethyl)amino-endo-tricyclo[5.2.1.0^2,6]deca-4,8-dien-3-one

Base Information

• Chemical Name: (1R,2S,6R,7S,1'R)-5-N-acetyl-(N-1'-phenylethyl)amino-endo-tricyclo[5.2.1.0^2,6]deca-4,8-dien-3-one
• CAS No.: 204275-05-8
• Molecular Formula: C₂₀H₂₁NO₂
• Molecular Weight: 307.392

Synonyms:(1R,2S,6R,7S,1'R)-5-N-acetyl-(N-1'-phenylethyl)amino-endo-tricyclo[5.2.1.0^2,6]deca-4,8-dien-3-one

Chemical Property of (1R,2S,6R,7S,1'R)-5-N-acetyl-(N-1'-phenylethyl)amino-endo-tricyclo[5.2.1.0^2,6]deca-4,8-dien-3-one

Chemical Property:

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Technology Process of (1R,2S,6R,7S,1'R)-5-N-acetyl-(N-1'-phenylethyl)amino-endo-tricyclo[5.2.1.0^2,6]deca-4,8-dien-3-one

There total 1 articles about (1R,2S,6R,7S,1'R)-5-N-acetyl-(N-1'-phenylethyl)amino-endo-tricyclo[5.2.1.0^2,6]deca-4,8-dien-3-one 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: 89.0%

acetyl chloride (75-36-5) + (+)-(1R,2S,6R,7S,1'R)-5-(1'-phenylethylamino)-endo-tricyclo<5.2.1.02,6>deca-4,8-dien-3-one (204275-02-5) → (1R,2S,6R,7S,1'R)-5-N-acetyl-(N-1'-phenylethyl)amino-endo-tricyclo[5.2.1.02,6]deca-4,8-dien-3-one (204275-05-8)

Guidance literature:

With sodium hydride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(97)10820-6

Reference yield: 92.0%

(1R,2S,6R,7S,1'R)-5-N-acetyl-(N-1'-phenylethyl)amino-endo-tricyclo[5.2.1.02,6]deca-4,8-dien-3-one (204275-05-8) → (1R,2S,3S,6R,7S,1'R)-5-N-acetyl-(N-1'-phenylethyl)amino-endo-tricyclo[5.2.1.02,6]deca-4,8-dien-3-ol (227941-43-7)

Guidance literature:

With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; at 0 - 20 ℃; for 6h;

DOI:10.1021/jo982498h

Reference yield:

(1R,2S,6R,7S,1'R)-5-N-acetyl-(N-1'-phenylethyl)amino-endo-tricyclo[5.2.1.02,6]deca-4,8-dien-3-one (204275-05-8) → (1S,2R,3S,6S,8S,10S,1'R)-4-N-acetyl-(N-1'-phenylethyl)amino-7-oxatetracyclo[6.3.0.02,6.03,10]undec-4-ene

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / 9-BBN / tetrahydrofuran / 6 h / 0 - 20 °C

2: 89 percent / N-iodosuccinimide / CH₂Cl₂ / 0.17 h / -25 °C

3: 100 percent / hydrogen / Ranei Ni / methanol / 20 °C

With N-iodo-succinimide; 9-borabicyclo[3.3.1]nonane dimer; hydrogen; Ranei Ni; In tetrahydrofuran; methanol; dichloromethane; 1: Reduction / 2: Cyclization / 3: Dehalogenation;

DOI:10.1021/jo982498h

upstream raw materials:

acetyl chloride

(+)-(1R,2S,6R,7S,1'R)-5-(1'-phenylethylamino)-endo-tricyclo<5.2.1.0^2,6>deca-4,8-dien-3-one

Downstream raw materials:

(1R,2S,3S,6R,7S,1'R)-5-N-acetyl-(N-1'-phenylethyl)amino-endo-tricyclo[5.2.1.0^2,6]deca-4,8-dien-3-ol

(1S,2R,3S,6S,8R,9R,10R,1'R)-4-N-acetyl-(N-1'-phenylethyl)amino-9-iodo-7-oxatetracyclo[6.3.0.0^2,6.0^3,10]undec-4-ene

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